Chuck The Tranny Slut free porn video

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Chuck walked towards a bar near to his hotel. He knew that Canal Street was the gay area of the city but he also knew that it was also the most lively area for pubs and clubs. And Chuck was happy and confident with his sexuality so he didn’t see it as a problem. Almost immediately after entering the bar and taking a seat near the corner of the bar area a very pretty and extremely busty young lady in a black v neck T shirt practically bounced up to him with a beaming smile. “What can I get for you?” She grinned. “Oh hi, a pint of.!” Chuck scanned the beer pumps. “Yes, a pint of Carslberg please!” He smiled. “Sure thing!” Said the girl and grabbing a pint beer glass started to fill it up with the golden liquid. “There you go!” She said planting it down in front of Chuck and he handed her a five pound note. She duly returned with his change with another beaming smile before going to serve another customer.

Chuck felt a vibration in his pocket and glanced down at his mobile phone. He sighed seeing the name ‘Donna’ on the small screen. Without responding to it he returned the phone to his pocket and looked instead at the pretty barmaid who was now serving another customer. Luckily for Chuck she was leaning down to retrieve a bottle of something or other on the opposite side of the bar and Chuck had a nice view of her shapely legs as her short skirt rode up at the back. Chuck was away on business in Manchester. But he and his wife, Donna, had fallen out just prior to him leaving home. The argument, as always, was over money, or the lack of it! Well tuff shit, Chuck thought to himself, I’m going to enjoy my evening out. He finished his beer and smiled as the barmaid came back over to offer a refill. With another beer in front of him he relaxed.

As the evening wore on and a few beers later, Chuck was considering going back to his hotel room to look at some internet porn and have a wank, just because he was bored really. But as he shifted on his bar stool he noticed a blonde girl at the end of the bar who glanced up at him. He was sure she had smiled at him. He quickly checked behind him in case she had smiled past him and seeing no-one else he smiled back. She quickly diverted her eyes to an empty glass in front of her and Chuck, feeling brave, having had a few drinks already, called the barmaid over and asked her to give the blonde a drink on him. The gesture was met by another smile as the blonde lifted her glass and walked towards Chuck. This was the first time he had noticed her but notice her he certainly did now. She was tall in her heels at around 5’ 10 and her long nylon clad legs ran perfectly up to a red mini skirt, topped with a black silk blouse and looking at the size of her chest, Chuck knew she was bigger up top than his wife, which definitely appealed to him. Chuck had always been a tit man and often wondered why he had married Donna who was only 34C. Fuck her, he told himself, as he thought of his wife again and felt a pang of guilt at not replying to her earlier text. He put Donna well and firmly out of his mind as his new ‘friend sat on a bar stool next to Chuck.

She introduced herself as Sam, short for Samantha and Chuck quickly forgot about his wife Donna as he listened to Sam’s sexy and charming voice, which intrigued him. She seemed very feminine and tender in her manner, aswell as being sexy as fuck, but it was the sight of the material tightly encasing her breasts that was the real turn-on for Chuck. He felt he was clearly much older than her, being 50 and she looking mid twenties. But hell, if she was up for anything he certainly would be, in more ways than one! Sam continued to talk explaining she was 27 and had recently split from her partner. The use of the word ‘partner’ intrigued Chuck and his imagination that it might have been a female partner got him even more excited. He ordered more drinks and they laughed, joked and flirted. And it wasn’t long before Chuck and Sam were kissing and gently touching. Chuck glanced at his watch noticing it was just after 11.

Still feeling brave he suggested that Sam and he might want to go somewhere more private and Sam giggled. “Private? Where do you have in mind?” She cooed at him. “My hotel?” Chuck grinned sheepishly before Sam reached over and kissed his hand gently. “C’mon then!” She purred and stood up to leave.

Thankfully the hotel apartment block was only 5 minutes walk from Canal Street and as Chuck turned the key in the door he felt the gorgeous girl behind him sliding her hand around his waist and down over his bulging trousers. He quickly walked into the studio apartment practically dragging Sam behind him and within minutes he had her pinned against a wall as she returned his deep passionate kisses. They broke off kissing and Sam smiled at him.

“Do you mind if we shut the curtains?” She smiled and Chuck quickly pulled them to, cutting out the light in the room but there still enough to see each other. “Now, I need to go to the bathroom. You get undressed and I’ll be back in the minute.” Sam said almost excitedly and within seconds Chuck was naked and rock hard, his 8 inches sticking up like a flag pole as he waited patiently in the double bed, covered loosely by a sheet. And if he wasn’t fully turned on at this point he certainly was when the bathroom door opened. The beautiful gorgeous blonde Samantha emerged dressed only in a black overflowing bra, matching panties, hold-up stockings and heels. Chuck nearly came there and then but Sam had other ideas as she dipped to her knees on the side of the bed moving on all fours towards her goal. Chuck watched her bra encased breasts swing and tremble as she moved towards him, her long hair hanging down around her beautiful face. His cock throbbed as Sam pulled the sheet back and reached out to slide a hand around Chuck’s massive rock hard cock shaft. She purred as Chuck felt her slide what felt like an oily hand up and down his hot throbbing shaft. And then in complete amazement he watched the beautiful blonde dip her head and run her tongue around the thick mushroom head of his cut cock before smiling up at him and then sliding her lips down over the head and shaft. Chuck moaned softly knowing that if this wonderful creature kept this up, he would be cumming in no time at all. She grinned again releasing him and stepping off the bed walked slowly around to the side in line with his head. Leaning down she locked her lips onto his and he responded to immediately, their tongues playing in the kiss and Chuck was very aware that his heavenly angel’s heavy breasts were now just above his face as she kissed him. As she moved lower, her body over Chuck’s, he tongue licked down over her chin and neck as he reached up to close his hands onto her big soft breasts for the first time. His cock throbbed immediately releasing pre-cum that he felt run down his rock hard shaft.

Sam’s lips and tongue ran down over his neck and chest as Chuck reached around to unfasten her bra and her big breasts tumbled straight down into his face. He watched her arms go backwards and sensed she might be removing her panties as his lips and tongue sucked and slurped at the fleshy mounds now being squashed into his face and mouth. Sam eased further down his body and grabbed his trembling cock by the base. Chuck still had his hands on her breasts as they dangled down over his chest and he reached his mouth up to tickle her flat tummy adorned only with a jewel in her navel. But Sam moved further down, her body now over his as he tongue ran over his tummy and ever closer to his cock head. He closed his eyes and reaching up ran his tongue over her pierced belly button as his hands concentrated on mauling her breasts.

Then he felt her hot mouth encase his cock head again and he gasped out loud closing his eyes, his hands still on her dangling breasts. Then just as she raised her stocking clad knees onto the bed either side of Chuck’s head she dipped lower almost deep throating him. He gasped again as he felt something slide over his cheek. He immediately opened his eyes and couldn’t believe what he was looking at. Dangling down from her new lover’s waistline was a massive cock head that was rock hard. For a split second Chuck froze, intimidated by the sight of a cock, so near his face and so big. But he suddenly felt the compulsion to lift his head and slide his tongue over Samantha’s cock. As he did he felt it twitch in his mouth and for the first time ever he opened his lips to take a cock between them. Sam let out a loud moan and sank her mouth lower down over his cock as he started to suck on hers too. This was totally new for Chuck but felt so right. Samantha was the most beautiful girl he had ever been with but with her cock too, this still felt so right for him. As he started to take it deeper into his mouth sliding it back and forth, Sam repeated the actions on his monster cock. Chuck was now only seconds from cumming. She clearly sensed this and eased off him before turning to look down at him, her blonde hair falling around her perfectly beautiful face. “Are you okay with this Chuck?” She asked innocently. But she could tell by the look of lust in his eyes that he had no problem with his new found friend having more to offer that he first thought.

“Have you ever sucked a cock before?” Sam said and Chuck shook his head. “Well, you are about to have your first cock!” Although in the heat of the moment earlier he had licked and sucked on her, fear suddenly filled Chuck as he realized that there was no turning back. Without waiting Samantha eased herself closer to Chuck’s face and reaching down with her hand pulled his head over to her massive erection. Chuck certainly knew he had no choice when Sam spoke next. “C’mon Chuck, be a good boy and suck on my cock like a good little cock sucker!” Soon her cock was back in Chuck’s mouth and with the pressure of her hand on his head and her moving her hips closer she was practically shoving the monster meat down into his throat. Although he was nearly gagging he sucked on it hungrily. And to his surprise it felt good and he liked the feel and taste. But he was nervous about her cumming in his mouth. Samantha didn’t seem to care and was now fucking Chuck’s face with a new passion and moaning with pleasure as she did her hands mauling at her breasts flesh at the same time. And seconds later she let out a loud moan as she shot a huge load into Chuck’s mouth and down his throat. But rather than choking Chuck was amazed at how good it felt. It was warm, salty and thick. He swallowed it all as Samantha, with her breasts trembling jerked her cock shaft, draining her balls and directing more cum down Chuck’s throat.

Finally she eased off Chuck and knelt on the bed with her heavy breasts dangling down. “You can fuck me now!” Sam purred with a smile. Chuck didn’t need asking twice as she knelt behind her, easing his thick cock into her open arse. As he had expected it only took a couple of strokes before his cock exploded up into her arse shooting cum deep inside her.

Then they curled up on the bed and slept.

Chuck awoke to see Samantha looking at him, her blue eyes shining in the morning sunlight that was coming through the curtains.
“Was that all new for you yesterday Chuck?” She enquired and he nodded. “Well I guess I need to teach you some more then don’t I?” She grinned and Chuck’s cock started to harden just at the words that his new lover was saying. She eased herself onto her back with her knees bent and feet on the bed. “First you can lick me down there!” Chuck watched as Sam eased her hands down to her arsehole looking up at him expectantly. Chuck felt nervous, it was one thing sucking a cock but anus licking had never entered his mind and he was reluctant, although he wanted to please his new lover.

“Let me show you!” She said. “It’s easy. Turn around and bend over!” Chuck did as he was asked and turned and bent forward so his bum was facing Sam with his head on the bed and hands resting on his knees. “Back up a little!” Sam said, so Chuck shifted his position. He felt her long nails on his arse as her fingers began to spread his cheeks. And then he felt her warm breath on his bum cheeks before her tongue made one long pass from bottom to top. Chuck literally gasped having never felt anything quite like it and his cock was hard in seconds. Sam repeated the action a few times before she started probing her tongue directly onto his anus. He let out a loud moan of pleasure again and felt his cock head ooze precum. He had never felt anything like this and his cock was twitching with every probe of her tongue. Chuck was sure he was going to cum again. He didn’t want that to happen, at least so soon and knelt up straight and turned to face Sam. She was smiling. “You like?” She grinned. Chuck leant towards the sexy blonde and kissed her passionately. “I’ve never felt anything so sexy!” He said between kisses. “Now it’s your turn!”

The gorgeous Samantha lay back once again, still dressed in stockings and Chuck took in the beauty of her body including her cock that was soft and lying to one side. She raised her legs and as Chuck bent forward dipping his head low. He did it exactly as Sam had done to him, with one long lick along the length of her crack and then back to her arsehole with the tip of his tongue. He felt her squirm and heard her moan as he began to warm to the task of pleasing her. Her fingers were in his hair and he realized he was so happy licking her arse. Feeling adventurous he began to alternate between long licks and probes. He kept the momentum going noticing that her cock was rock hard again. Reaching up a little he began to lick the shaft all the way up and down running his tongue up the base of the shaft to the helmet and back. He tasted her skin and loved the feel of it and the taste of her precum on his lips.

“I want you to fuck me right now!” Chuck heard Sam almost scream and he immediately stopped licking and grinned as he rose to his knees and leaned forward for a deep kiss. She raised her legs again, higher this time so that her feet were resting on his shoulders and he could feel the silky smoothness of her stockings against his chest. Reaching down Chuck felt Sam’s hand on his cock guiding it towards her as she whispered. “Fuck me hard baby!”
He pushed gently forward and felt tip of his cock sink into her tight arse. He hesitated as he felt her anal muscles tighten and relax around his cock tip and then he pushed forwards again and his cock sank all the way to the hilt. Sam left out a loud sigh and reached up to place her hands on her breasts, squeezing and pulling at her nipples. Chuck began to move with a rhythm. Sam was tight and since Donna would never let him fuck her arse, this was new to Chuck. He was in heaven convinced this was the best fuck he’d ever had. He was turned on by her playing with her own breasts and reached his hands down to join hers. Immediately she released them and slid her hands lower to cup his balls with one while her other hand probed his arse.

Now and then Chuck leaned forward to kiss and Samantha, as the beautiful girl with the big cock urged him on whispering directly into his ear or sticking her tongue in. This sent him into another dimension. Finally Chuck came with long spasms that ran through his body that he thought and hoped would never end. He felt drained but happy and was still hard inside her as she took his head in her hands and kissed him deeply. He felt another twitch or two and then he was really done.

“Now it’s my turn!” Samantha said and smiled.
“I’m not sure!” Chuck suddenly said looking and feeling very worried. Sam simply smiled at him. “You weren’t sure about sucking my cock!” Chuck nodded in agreement. “And you weren’t sure about rimming!” Chuck nodded again.
“Listen Pau!” Sam smiled affectionately. “There’s no hurry! Lets get into bed!” and see what we get up to.

Chuck slid in beside the beautiful busty blonde with the big cock and pulled the duvet over as the two lay together holding each other. Chuck was lost in the moment of pure lust and emotion and as he felt her soft warm curvy body next to his he found himself getting excited again and his cock began to grow. Sam could feel it growing against her own erect cock. As Chuck nuzzled her big soft breasts he could feel her cock against his tummy and he reached down, first to hold it then pushed it between his thighs. It felt good as he eased up the bed a little. Almost immediately he felt Sam’s hands run down his back and ease into the crack of his arse. Moments later she was fingering his arsehole. And then there were no fingers, Chuck suddenly felt the distinct shape of the head of his lover’s cock pushing gently against his anus.

“Just relax baby, it’ll feel good!” Sam said as she pushed it in further. Chuck felt an initial feeling of pain then it was all pleasure. He just felt full at the back!
“How does that feel babe?” Sam asked and Chuck simply locked his hands onto her fat breasts and his mouth onto hers in a passionate kiss. She began to move back and forth ever so gently and Chuck relaxed even more. He even found himself looking forward to the thrusts and began to move his hips back to meet hers and feel her cock as they got the rhythm going. Samantha was facing Chuck and slightly lower and he had his legs lifted around her hips with his rock hard cock squashed against her tummy. Chuck just thought that Sam looked gorgeous as she humped his arse. She slipped out and then Chuck felt the tip of her cock at his opening again and the gentle push as she entered him again. When she began fucking him now, it was deeper than before and Chuck loved this treatment he was receiving from his lover. Her eyes were sparkling as she began to fuck him harder and her breathing became faster. Chuck was caressing her nipples as she gasped. Then she was cumming inside him and he could feel each spasm and twitch of her cock and felt like she was cumming forever and filling him up.

For Chuck, it was a fantastic feeling. Indeed a night of fantastic feelings and he knew that there would be no going back. Samantha, exhausted by her exertions collapsed on his chest and slid her hand between them to give his cock a hard tug as she felt the hardness again. He pushed her over onto her back and slid up her beautiful body as she continued to jerk him. Moments later he was shooting stream after stream of hot cum that splattered her heavenly chest and nipples. Chuck didn’t need asking twice and immediately dipped his head to lick the cum from her breasts before sliding his tongue back into her mouth in a spermy kiss.

And once again they slept. When Chuck awoke his new lover was gone. He thought he would never see her again.

“Where the fuck did you learn that!” Donna smiled at her husband and Chuck grinned back. “That was amazing.I’ve never had my arse licked before. God I am horny. Give me that cock of yours!” She smiled, and Chuck did over and over again.

2 Months Later

Donna smiled as she took the wrapped package from her husband. “What is it?” She grinned. “You’ve already brought me all the lingerie?” She glanced down to see the array of sexy lingerie. Chuck simply grinned as Donna opened the package to reveal an 8” strap-on dildo. “Oh my god!” She laughed just as the doorbell went. Chuck immediately went to answer the door and came back into the bedroom accompanied by a gorgeous blonde in a red mini skirt and black top. “This is Samantha!” Chuck smiled. “And she’s come to play with us!”

Donna simply smiled!

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Heather's dress or lack of was amazing. It was white and floor length in the back. It was open down far enough exposing half of her tight ass. The front was cut open down to her naval it was covered in very sheer lace, so the inside of her tits and her cleavage were easy to see. From her waist down, it was also open. She was wearing a sheer G-string. She must have been excited because you dick was semi hard and it really filled out her panties. If you looked close enough you could see her dick...

4 years ago
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Chuck and Me

It was a difficult situation. On the one hand I owed the man my life and on the other the same man had just ruined my life and I wanted to kill him. Oh God did I ever want to kill him. I'd known Chuck damned near all my life. We grew up three houses from each other on Delancy Street. We went to school together, dated the same girls and played on the same teams. We were closer than brothers. He'd had my back and I his any number of times and everyone knew that if you fucked with Chuck you...

3 years ago
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Chuck And Sue Always Hot And Ready To Fuck

Chuck and Sue had been married for several years, and they were still as hot as firecrackers for each other when it came to their sex life as man and wife. Unlike many couples, both Sue and Chuck were very attractive and they were certainly very attractive to each other. Chuck still found his sexy wife as hot in bed and as sexually desirable as he ever had. He loved to play around with Sue, play with her body, kiss and caress her, and he always loved it when both of them took their sexual...

3 years ago
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Chuck and LisaChapter 10

I woke up being nearly smothered by good smelling women. The weight on my stomach was Tiani, and Brandy was on one of my shoulders. The other shoulder held Nancy, who was whispering in my ear, "I love you, Chuck. Please make me a mommy again. Please, Chuck. Let me give my mom another grand baby." I kissed Nancy and told her, "Let it happen when it happens. Let's not force anything and let this next one come on his or her own." "But this is the perfect time to do to it, Chuck. It'll...

3 years ago
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Chuck and LisaChapter 20

Someone was giving me lots of kisses so I reached up pulling her to me, thinking one of the girls wanted some middle of the night loving. As I held the tiny body to me, Tiani said, "Wake up, Chuck. Your phone is going crazy over on the nightstand. It rings and buzzes and keeps ringing. Whoever is calling calls right back when it goes to voicemail. Answer it, Chuck, it must be important." I crawled out of bed and reached for the phone to look at who was calling. The phone began its ringing...

3 years ago
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Couple Finds Another Plus Tranny

While I was in the military, there were many opportunities to see some of the wild and crazy sites and people of the world. One time in Japan a bunch of us in a mixed group (men and women) went to a show that featured transsexuals. These were men who now dressed and acted like women. All of the men/women featured had breast implants to additionally make you believe they were real. The show was very exciting with each of the trannies on stage showing us they were as good looking without their...

3 years ago
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  • 36
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First time with a Tranny

Stevie had always found it relatively easy to get girl friends. Not all had been good experiences. He always felt that after sex he just wasn’t satisfied. Maybe he wanted something different. Some people are perfectly fine about being gay or bisexual, but for others, it is a scary mine field. Stevie was one of those people. People had commented on him being gay for years and he always felt ashamed. He denied it, of course, but as time went by the thoughts about the whole subject haunted him. He...

Gay Male
4 years ago
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Chuck and LisaChapter 35

Flying home with Lisa sitting next to me after telling me that she was pregnant had my head spinning. Thank goodness being on mental autopilot reminded me call in to enter the landing pattern. I released my seat belt and leaned over to Lisa when we finally landed, had the aircraft shutdown, ready to refuel and put in a hangar. "Don't give me news like that while we're flying and I can't reach over to tell you how crazy in love with you I am. This is big, really big." Lisa smiled and...

4 years ago
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Chuck and LisaChapter 41

The weather decided to give us a fit on the sixth day into our voyage sailing to Hawaii. Steve was on the wheel in the indoor cockpit when he sent Judy down to wake me up. Steve showed me the disturbance that was swooping down on us when I got up in the saloon helm with him. He asked me what I wanted to do. "You've had more experience than me, Steve, but everything we've learned is to take the sail in, start the engines, and keep our bow into the seas." "Yeah, that's what Dewey taught...

3 years ago
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Chuck and LisaChapter 53

I knew I hadn't done anything inappropriate with Cassie, and felt good about it, when I went downstairs this morning. She didn't need to be teased into thinking I would take her. As beautiful as she is, and as really sweet as Izzy is, I didn't want Cassie to think I was going to take her in with the rest of my ladies. Mina gave me a hug when I walked into the kitchen, and said, "You were so good to our Katrina. She told me she thought you gave her a baby yesterday. She also said you were...

3 years ago
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Chuck and LisaChapter 69

I woke up early enough to almost beat Dewey to the bar. He was making up the mixture of the morning’s libation. I said, “Ah, Dewey, I probably shouldn’t have one of these this morning. I’m probably going to have to be one of the pilots to get us home.” “Not a chance, we had two crews on the aircraft to get here, and only one crew is going to be flying your Citation home. We’ll still have a backup crew on the airplane with John, Wanda, Lisa, and Brandy.” I told Dewey, “I didn’t know Wanda...

2 years ago
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Chuck the Cuck

Chuck the Cuck The most complicated diversions of our lives can begin with something simple. A wrong turn. A misdialed phone number. A car wreck up ahead by a total stranger. We are leaves in the wind. We are tumblers in a safe. We plot, and we plan, and we scheme. And in the end, it is simple chance that gets us. For instance, there was that might at Applebees, when my husband Charles and I met for drinks after work. If we had gone at another time, or to another restaurant, all of...

2 years ago
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Chuck and LisaChapter 16

I awoke early once again, and was able to be on the patio outside our suite to watch the glow of first light on the horizon. Hands snuck around me again, and I pulled the owner of the hands around to sit on my lap. The two of us didn't speak, but we mentally joined as we both enjoyed the closeness we shared. It wasn't unusual that we heard Missy or Mercy say something to us as we sat together, but we often heard from the triplets, Marion and Virginia, or Aunt Etta. Our lives had another...

1 year ago
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Young Tranny at Great Grandmas Funeral

“What’s going on,” inquired the 34 year-old construction and building inspector.“Nothing,” smiled the high school senior with the 22-inch dark brown wavy hair extensions and gray contacts. “What’s up with you.”“I want summa that.” he leaned forward trapping her between his heaving chest and the counter.“What?”“That sweet potato pie over there,” he winked.“Oh, okay! I’ll cut you a piece.”“You do that,” he said not moving an inch and running a forefinger down her weave.She darted her eyes away,...

3 years ago
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Threesome with a tranny and a woman

I have a friend with benefits that I have been with for a few months. Her name is Bree and she is a tranny. I figured out I was Bi a few years ago so I started looking around for guy's to have sex with. Like others, I found guys who seemed to want to get together but would not pan out for some reason or another. That's when I discovered tranny's and new I wanted to be with one. So I started to look around for one and that's when I met Bree. She was beautiful 5'3" tall, dark hair and a tight...

1 year ago
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Nate and his tranny neighbour

My first ever story. Depicting sex between a man and a transsexual.It is lengthy but personally I enjoy these best. Constructive feedback is greatly appreciated, so feel free to write to me. Enjoy ; )Nathan (Nate for short) was an average eighteen year old boy; liked girls, sports, partying, and being on his summer holidays he enjoyed the time off school. With some exceptions to the average rule, he loved his kinky dirty thoughts and porn. Frequently watching shemale porn, gorgeous busty women...

1 year ago
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My first but not last encounter with a tranny

My Wife and I have been married for about 3 years now and have since recently, been looking to have our first experience with a she male. I met a girl online name Judy and after chatting for a while and exchanging pictures we agreed to a meet and greet. Judy proved to be a very sexy transgender with feminine features. Her highlighted hair was long and she had size B cup breast with a thick firm ass and long pretty legs. She was very beautiful and had an awesome personality. We sat down and...

She Males
4 years ago
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Chuck

“You ought to be sleeping at legitimate hours.” A private message from Chuck, 221 am. “Trust me, I wish I could, but my body is convinced it’d rather be doing something else but sleep. There’s hardly anything I can do!” “There’s only one thing you should be doing at this hour. And it shouldn’t involve being online.” I paused and smiled to myself. Chuck is the assistant coach to the tennis team I joined at the country club. He was nothing like the rest of the eager male morons trying to flaunt...

Straight Sex
1 year ago
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Chuck and LisaChapter 48

I needed to unload and went to the bathroom with the help of my peg. It was early, but I needed something for my mouth. I went to the other end of the hall of the women's private spaces and into my big bathroom. I thought another forty winks would be good after brushing my teeth, so I went back down the hall to get back in bed. People had moved around and Zena was nearest the outside of the bed. Zena wrapped herself around me when I slid under the covers, and whispered, "I think I'm ready...

2 years ago
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Chuck and LisaChapter 63

Tiny Izzy was sitting on my chest giggling at me while Nitika was leaning over my head trying to pry my eyes open. The two darlings were jabbering away with each other, probably trying to decide what to do with me. Cassie and Nancy were watching the two to make sure they weren't going to be too rough. I reached around both little girls and brought them to me so I could smooch them with kisses to make them giggle even more. I realized it was important for me to get up when Nitika very...

4 years ago
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Chuck and LisaChapter 75

I knew when it was time to get up because the girls in bed were getting restless and I had to use the bathroom. I slipped my peg and shorts on as quietly and quickly as possible, and made coffee before going outside to do my forms. To me this was the way I should begin my day. This was how I healed myself and how I prepared myself for the day to come. There were a lot of people who joined me in getting ready for today, even though it was Saturday and they didn't need to get up early. The...

3 years ago
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Tranny Wife Me

I have always loved sex with trannies, even more than sex. Friendship and closeness that I would struggle to fin in a guy. My wife had no huge preference for Tgirls but she did have a ravenous appetite for sex and was curious enough to try everything. We decided to go to Manchester and their regular Saturday night Tranny evenings and from previous visits, we had a few drinks in Napoleon's Lounge. It was a popular meeting place for "girls." Trannies who liked other girls, trannies who preferred...

4 years ago
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Chuck and LisaChapter 31

The family had no trouble settling into the beautiful suites at the resort. Jane came walking up from the outside almost as soon as we were enjoying the open patio doors. She said, "See how easy it would be to get to you guys? I don't think you have anything to worry about, but remember your vulnerability if something comes up." All the women, including Tina, swarmed the Japanese/Hawaiian beauty. We all noted that an additional low fence had been added between our patio and the swimming...

1 year ago
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Chuck and LisaChapter 32

The meeting went very well. We kept going over the drawings and plans, making notes and expansions. I told the architect that I wanted him to talk to Mark in Costa Rica and the architect who put that place together. I told Katana, "You should go with him to take a closer look at the place. I want that same quality here at this resort. I know that place is a palace, but I want that in the new resort too. I want the guest areas to be so plush that people will want to be there. I also think...

3 years ago
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Chuck and LisaChapter 37

I really didn't know what to expect to hear from Margaret Boon, a Marine, and former driver who I had served with. We hadn't been close over there, and I don't remember her being close to anyone. I really didn't have any close friends either, so Maggie, as we knew her, and I weren't that different. We weren't unusual, as everyone there had to deal with where we were and what we did on their own terms. The fact that Etta and Julie were included along with Lisa, Tina, and Jane, in this...

3 years ago
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Chuck and LisaChapter 39

After being relieved by Steve, I made the mistake of going into the saloon to find the kids gathered and playing some of their Lucky Lady Blues Band music. I couldn't sneak past Bonita, and when she saw me, she hollered, "Come finish this piece so I don't hear it in my sleep any longer, Chuck." What can you say to Bonita? She is all Sharp and a product of the headstrong Kathy. I headed to the instrument cabinet knowing there would be no rest until this one piece was completed, written,...

2 years ago
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Chuck and Maggie Naked in SchoolPart 6 SaturdaySunday

For the second morning in a row, I woke up in a guy's arms. More amazingly, it was the same guy. Most amazingly, it was my boyfriend! Boyfriend. Me. What a stunning turn of events this was! I was all hunched up into Chuck's chest when I woke up, so I kind of flicked my eyes upward to get a peek at him. He was still sleeping. Hmm. What an opportunity, yes? That was kind of something I'd dreamed about. As I've said, back when I was Little Miss One-Night-Stand, sleeping over just wasn't...

2 years ago
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My first tranny

I had never been with a tranny before and did not plan on being with one at all but you never know what will happen. I had a bad day, I had been in meetings all day with new clients in another city. I decided to stop for a drink or two before going back to my hotel room. I found this bar that look interesting so I went in. There were lots of beautiful women there so I thought that maybe I would get lucky and not have to be alone tonight. I went to the bar and ordered a drink and checked out the...

3 years ago
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My first time with a tranny

I always had a strong sex drive, and since I had been around 16 I had been turned on by gay porn. I must say that I am straight, well on second thought, better say that I am bisexual. And I always have and will like girls. But there is something about a cock that turns me on and I then discovered shemale porn. I think that a hot sexy shemale and a cock is the best combination there could be. I have a strange fascination with cocks and a hot sexy girly body tops it off.In August 2007 I was 24...

1 year ago
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Dream Tranny

Dreams can be strange, sexy things. Your wife may be a stunning knock-out, way the fuck out of your league, but I bet she ain’t your dream girl. No, your perfect fantasy angel has the big tits and pretty face you love so much, but she’s also got something extra: a big ol’ dick between her legs. Sorry, wifey, but tonight may be a good evening to spend with DreamTranny.DreamTranny.com is a site with history. They’ve been around since 2000, making them one of the older shemale porn operations on...

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3 years ago
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Chuck and LisaChapter 4

Morning came too fast for me. Lisa was equally groggy as she rolled on to her back and whimpered, "Do I have to get up?" I told her, "Let's get up and have breakfast with everyone, but we'll put off going home right away and maybe not even today, so we can get some rest. Come on, up and at 'em, Baby." We quickly showered and went downstairs to chat with the ladies and hold the kids as they came by. John and his family showed up with Gene, who announced that it must be time for...

2 years ago
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Chuck and LisaChapter 21

Morning brought the happy sounds of the little ones jabbering away in their cribs before the adults rescued them from their confines. It's funny to look at all of those cribs with little ones standing at the sides jabbering at each other. Our kids were amazing since they weren't fussy and didn't cry much. The adults were smart though as we quickly attended to the little ones when we awoke. It's funny how those of us who weren't mothers helped those who were so it allowed for each of the...

4 years ago
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Chuck and LisaChapter 27

Lisa and I woke up just after five and went straight to the gym room and did a thirty-minute workout. Our next stop was on the grass outside to stretch, but it was raining hard, so we stripped under the overhang and ran to the pool for some cardio work. We were laughing and having a good time when we went into the house to get a shower and dressed. Tina approached us, stark naked, and said, "It's not fair; I didn't get to work out or swim with you. Make me swim for a little while, then...

2 years ago
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ChuckChapter 2

Even though I wasn't in the mood, my friends and I celebrated our bowl win. Willard told me I would just have to get over Sammy and get on with my life. I knew he was right and I hooked up with an Asian woman at the party and just had some raw sex. It felt good, but it wasn't Sammy. Since football season was over, my three friends and I decided we would put our savings together and open up our two exercise gyms. Tony and I had already earned certificates in physical exercising. We were...

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