Caitlin Knows Best
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Rediscovering Caitlin ? by: Lisa Grey Chapter 1: Discoveries "I can't believe I agreed to do this," Lynn groused. "Oh come on, Lynn. It's not like anybody is gonna see you," Janet half teased, half soothed. Janet looked at her boyfriend. Lynn stood there in the doorway of the bathroom in their hotel room, his below-the-shoulder length brown hair dripping from the bath he was just in. Lynn was not the most masculine guy on the planet to be sure. He was slender, his 5'6"...
This story is an idea I worked on recently. It comes AS IS which means there are mistakes I’m ignoring because laziness. (Hehehe… Yeah. I’m lazy.) For my stories that I HAVE edited thoroughly, see Beginning Anew or any of my stories that don’t ahve the AS IS prefix. P.S. I liked this idea and wanted to continue it, so if you, my readers want me to, I will edit it and write more and release it again as an official story. But only if you as readers want me to, otherwise, I will write ideas as...
Another fantasy with my young associate.I asked Caitlin to join me for a large multi-day meeting among defense counsel at a large hotel in Virginia. I explained that it would be a good experience for her. I had arranged for adjoining rooms in our hotel so it would be easier to discuss the days’ events. During the first day of meetings, Caitlin and I sat together so we could talk. Caitlin was wearing a very conservative blue suit and a white cotton blouse. She looked very much like a lawyer I...
The night that things got out of control and went farther than I ever imagined they'd go, I was left with a sense of wanting so much more.Caitlin and I had been talking, joking, having a good time, doing some harmless flirting, and that evening she'd gone upstairs, leaving me hard as a rock, horny as hell, and masturbating like a horny fool in my living room watching porn. When I was finishing, Caitlin had come downstairs, walked in on me just having finished having a massive orgasm in a paper...
Teen"Whaddaya think," I replied, nonchalantly. "GET OFF HER RIGHT NOW, ERIC." Blah, blah, blah, I thought. I got to and began drawing my dick out of the pussy it had inhabited... The tight little pussy I'd been pumping to oblivion before Samantha came in... The pussy of our ten-year-old girl. "NOW, YOU SICK BASTARD!" "The more you talk, the longer I'll take, Samantha," I told my wife, with a smug grin on my face. Pulling myself further and further out of Caitlin, I stopped the second...
I adjusted my sunglasses as I peered over the top of my newspaper. The warm August sum was making one of it's last stands as the summer was coming to a close. I watch as Caitlin and her best friend Samantha enjoyed the last weekend before the start of another school year. Samantha lives next door and I have watched her grow from a snot-nosed little brat into the fine young lady that was about to start her Freshman year of college. I watched as her and Caitlin laughed and jumped around in the...
IncestAfter making love on the beach, we took a long swim in the ocean to wash the sex off. Caitlin left the water first and I could only marvel at her amazing body. Her swimsuit wrapped her butt perfectly and that made me crazy with desire all over again. She turned to look for me and her huge blue eyes beckoned. I loved seeing her breasts poking through the thin fabric of her suit; small boobs at 34B (the same as me on a good day) round and perky with very visible nipples. It was getting on in the...
Caitlin had just turned sixteen, and for a girl her age, all I could say was, "Holy shit. What a fucking body on her." When she came over to the house the day after her birthday, she was hanging out with my daughter Kayla. They were on the back deck and I heard the girls talking about going swimming. I was in the kitchen getting a snack when Kayla came into the kitchen. "Can Caity and I go swimming?"I know we'd talked about going out somewhere and getting some dinner but we decided we'd...
TeenI sat there in my computer chair, a paper towel in my hand, and my dick limp. I had just finished watch a porn video of a guy and a girl fucking, had fantasized about having sex with my step daughter's best friend Caitlin, and I'd cum so intensely hard that I couldn't see straight.What I didn't know was, as I was doing this, my step daughter's friend Caitlin had walked into the living room in her bikini."Oh God, Mr. D. I didn't know you felt that way about me," Caitlin said.And I felt like a...
TeenCaitlin Forscutt to all observers, seemed to be the perfect innocent schoolgirl. Intelligent, quiet and reserved, Caitlin didn’t go out of her way to attain high-school popularity but neither was she ostracized as a loser. She didn’t go looking for male attention, but it found her anyway. For many sensitive young men, she was their first unrequited love. Caitlin’s milky white skin and perky boobs were the fuel source for many a masturbation session. She took this male attention in her stride,...
Throughout high school, I would normally doodle on my pages. I loved art, but not really the realistic type. I loved cartooning, and did it quite regularly. I did it all through high school, and this made it difficult to keep high grades. But somehow I made it through, The Arts and English being my top subjects. With those high eighty to ninety percent marks, I went to an art school in Tokyo. I figured I needed the experience in order to pursue a career in cartooning or illustrating. So I...
Caitlin woke at 6 AM and quietly rolled out of bed. She realized Devon must have been as tired, as she was the night before based on the fact he didn't wake her through the night to pleasure him. She laid out his clothes and slipped out the door into the long open hallway. Her room was next to Devon's and there was a door joining the two but they rarely used it. The door had one lock on Devon's side so he could enter her room at any time. It hadn't happened since she had been there. Even...
Caitlin and James - Part three By Cherie Petersson Chapter nine James dozed off to sleep soon after we had sex. I lift up the covers and admire his naked body. It's not that muscular, but it is well toned, quite beautiful in a sort of androgynous way. The condom is hanging off his spent penis, threatening to fall off, I remove it and grab some tissues and wipe his penis. He stirs a little but stays asleep. Poor guy, he must have got up very early to get his hair done and...
Thanks to everyone who read Parts I and II. I especially want to thank those who voted and those taking time to leave a comment. I hope you enjoy this part—it’s a fun one. Maddie ~*~*~ Part III Working on the House For a couple of weeks while Jon was at work, Catie worked at the house. She cleaned cabinets and floors and painted the each room. Jon would drop her off every morning and return in the evening to pick her up. Sometimes they would go out to eat. Sometimes he took a change of...
Dullichan: from Celtic Mythology; a headless black rider, death follows where he stops That tongue swirling around her swollen clit was nothing short of heaven itself. As it twirled round and round so did her thoughts spin round and round cycling from pleasure to passion to pleasure again in Caitlin's expanding consciousness. She lay there breathing heavy, moaning, letting herself freefall deeper down the rabbit hole of ecstasy abandoning reason if just for a season... Caitlin awoke that...
SAVING CAITLIN by MaddieKim Again I want to thank everyone who took the time to read this story. I appreciate the comments and the votes. I thought if one person likes this tale then I’ll have done a good thing by submitting it. It seems more than one of you liked it, so again I say thank you to each and every one of you. Maddie Part IV Back to the cabin When she saw the car coming up the drive, Ginny bolted out of the cabin and flew into Jon’s arms the moment he was out of the car. He...
I'd tried to walk around Caitlin as she stood in front of me. I couldn't do it without brushing her, and moving up against her. I could not believe this was happening. She'd literally just walked into my living room at the end of me watching porn and jerking off into a paper towel. She was so chill, mellow, and not the least bit embarrassed. I on the other hand felt like a total fucking tool.After a conversation that lasted a couple of minutes, I got up and moved out of the chair. She stood...
TeenThe girls thanked the driver and made their way back to the house. Devon met them at the door to get his report from Paige. He could always tell when his trainer engaged in sexual contact with his slave. Her eyes reacted like a magnet with opposite poles turning away as soon as he looked at her. Devon motioned for Caitlin to wait in the study while they spoke and without hesitation she left the foyer. "Did you enjoy yourself today?" He asked with a teasing grin. Paige's face became even...
"I have a surprise for you!" Devon said as he burst into her room. "I hope you'll be as excited as I am." "Master, what are you talking about?" "Come here, sit with me." She sat next to Devon on the king-size bed smiling in anticipation. "I just got off the phone with Gregory. It seems he's come across a new trainer for you. The boy is supposed to be fantastic. And, it gets better." She could feel the energy radiating off of him. She hadn't seen him this excited in quite...
Hi, To all Iss reader this is my first story hope U all would like it a complete fiction.my self raj i live in Mumbai this story is about my aunty nandita,let me describe her she is in her 30s,lives with her husband and daughter.She is born beauty with an awesome fig of 36.28.40 ..her assets are her huge melons of 36 d and her ass that will give a hard on to any guy who looks at it So now my story starts this was like 5 years ago when I was appearing for my 12 th HSC examination at that time my...
Ed looked at the guide as he flicked through the channels on TV. There was nothing that caught his eye as the clock on the mantel chimed out 9pm. " There will be something to watch soon, Caitlin will be home ." He mumbled as he switched the cable off and headed to his workshop. Ed had a small computer repair business that he ran from his house. He knew his way around computers and over the years he has managed to place hidden cameras in the shower stall and Caitlin's bedroom. He turned on...
IncestSarah called me midday. "You ready for Caitlin?" "More than ready." I answered. "Yeah. Leslie told us how she stood you up." "Oh, she had her reasons." I said obliquely. "Well, I think she should have gone through with it. She knew she had a boyfriend when she agreed. But you should have seen the other girls when she described her multiple O's. Even I was jealous. Wow. Crissi sounded like she was thinking about it now. Shelby turned pale. I think she's changing her mind. Pretty...
"You did amazing tonight, thank you for being so obedient. I know how difficult it can be." Caitlin smiled at Devon, she was physically and mentally exhausted and wanted nothing more than to lie down and go to sleep. Devon lit some scented candles and built a fire in the fireplace. "I realize you are tired but I'm afraid the events of this evening have me rather worked up, run a bath and prepare my nightclothes I want some time with you before you go to sleep." Caitlin nodded and...
After showering and getting dressed, Caitlin met Devon in his room as requested. It had been a while since they had time for a sexual session like they used to have. The paddles and restraints sat idol for months since Devon's promotion to Director of the society. He spent less time at home and more time taking care of the urgent tasks needed to keep everything running smoothly. "Caitlin before we begin, what was the name of the man you ran away from?" "Robert Angst, why do you...
His erection was buried so deep in her mouth it felt as though he would coat her brain with his orgasm, and she wanted that. She wanted that more than she had wanted anything ever. That was the new thinking going on in Caitlin's new mind. She was on all fours leaning over the back of her bed. The hand made of solid shadow held her head firmly. The heat that radiated from that strong hand penetrated her mind and its fingerprints were certainly imprint themselves on her soul. And she marveled...
Caitlin and James - Part two By Cherie Peterson Chapter five "Oh Caitlin, he's getting so excited about going on a date with you." "He begged me to go shopping with him for a special outfit for your night together. He even wanted to get some nail polish, special lingerie, a nightie and a negligee. I think he's expecting to get lucky," Justine says with a wink. Justine and I are on the train and she is telling me about the preparations James is making...
Caitlin and James By Cherie Petersson He was wearing pigtails and large hoop earrings when I first saw him. He's absolutely adorable. Maybe I should introduce myself first. My name is Caitlin, a few months ago I split up with my latest boyfriend - another in a long list of bossy macho males who saw me as a potential trophy wife and wanted me to put them first and me second. Well my ambition isn't to be a trophy wife, I love my job, I'm excellent at it, so why should I sacrifice...
After we cleaned up the office and put our clothing back on Caitlin and I walk out the office toward my car so I can drive us to grab dinner and back to her place. As we were walking to my car all I can think off is how much fun I am going to have tonight with her.....When we got to her place after dinner we sat in the lounge drinking some wine and chatted for while before she excuse herself to the bedroom. After about 5 minutes or so she reappear with just a bath towel wrap around her tiny...
Caitlin and James - Part seven Chapter 20 - The skirt debut - Jamie at work After I finish my first court hearing of the day I go to a waiting room and take off my wig and check my phone, expecting messages from assistant Felicity. There are text messages from her but my attention is caught by one from my lovely Jamie who is wearing a skirt and heels at work for the first time today. Jamie texts: "Haven't been made fun of yet but work is awfully busy - I'm on my morning 10-min...
Part II The examination ‘I want you to make sure she isn’t pregnant. I don’t want her to have to live with that. He was such a bastard to her.’ ‘I’ve already had her give my nurse a urine sample and we should know the results in just a few minutes. I’m going in now to give her a complete exam.’ ‘I’m going with you.’ ‘Now, Jon, why don’t you just relax here in the waiting room? She’ll probably be more comfortable with you out here.’ ‘No, I’m going in. I think she’ll be more secure with me....
A handsome man with salt and pepper hair greeted Devon at the entrance. His posture and strong handshake gave the impression he was very important. "Devon! How are you? It is great to see you again." The man said in a loud booming voice. "Sir Gregory! You look wonderful." The men embraced, patting each other on the back then released the hug and fell comfortably into a handshake. "Devon, you don't have to call me Sir anymore, remember?" Sir Gregory laughed. "Old habits die hard I...
"Can I have your attention please?" The MC asked trying to settle down the crowd before him. "I have the list of names for the annual slave competition. I'm sure you are all anxious to hear who will compete for this year's prize." The microphone squealed as he leaned close to it announcing the rules and names that had been chosen to compete. "The Master of the slave who has the most points at the end of the evening will win an all expense paid trip for two to Fiji, including a rental...
Halloween was today and Caitlin was looking forward to her sister Erin's visit. She woke up this morning feeling very well rested. She was becoming more comfortable and accepting of the transformation which had taken place within her. She had an understanding, a knowledge, that her transformation was more that skin deep. Her hair was how a crimson red, and her chest had settled into a thirty six D and her height was six foot. She had grown two inches in five days. She was more accepting of...
If you’re looking for a ‘stroke’ story, this probably won’t be for you. If you want lots of sex in every conceivable way, it may be better to go to any one of the other amazing stories by very talented Lit authors. There is very little of that kind of story here until later. If you hang around, your need for a sex fix will be satisfied. I do promise submissions will come fairly quickly. If you decide to stay, I hope you enjoy. All comments welcome. Maddie. I want to thank all of you who read...
Caitlin and James - Part six Chapter 18 - The skirt debut - Getting ready I wake up and give my darling Jamie a squeeze. I fully open my eyes and realise I'm hugging a pillow instead, that's why it it felt strange. I look around - yes I'm in Jamie's bedroom, but where is he? Today's the day we go into his office and ask about him wearing skirts and dresses to work. I can't hear him, he hasn't panicked and left has he? I lie back down and think. A few moments later I hear...
My eyes adjusted to the streaks of dim light that pierced the bedroom window. As they focused in, I saw the look of wonder on her face as she knelt between my thighs. She was holding my hard cock in her hand as she examined it closely. I felt her breath on my balls as she moved the head closer to her lips. As our eyes made contact, she softly whispered "Morning, Daddy. I didn't mean to wake you." I felt her rub her panties over my balls as she parted her lips and moved closer to my cock....
IncestSilence filled the house as I opened the door and crept past Caitlin's room towards the laundry. I quickly deposited the panties in the hamper and headed back to my room for a good nights sleep. I settled in and drifted off to sleep. I was awoken by the movement of my pillow. As my eyes adjusted to the dim light emitted from the alarm clock, I noticed her crouching beside the bed. "Caitlin?" I asked as she jumped and quickly sat on the edge of the bed. "What's wrong, Princess?" "Daddy, I...
IncestThe crimson haired beauty was facing the wall wearing a blindfold made of impenetrable shadow. Kneeling on her bed her arms outstretched and lashed to the crossbar of her large brass bed. She waiting once again for the lash of a whip crafted from the spine of a man. Feeling that whip strike her tender offered ass and go straight through her body and scream its way through the pleasure playground her head had become. Each lash was its own climax within her. She arched her back and lifted her...
Caitlin and James - Part five Chapter 16 - Reluctant witness for the prosecution As I drive home to James' place, I wonder if he went through with his promise. He probably didn't, because it's difficult to raise, he gets nervous about drawing attention to himself, but really, wearing a skirt would be such a small step after all the other stuff he does. Handbag, earrings, girly hairstyles, make up. I don't blame him for being nervous, then again I'd be angry at him breaking a...
Caitlin and James - Part Four By Cherie Petersson Chapter 14 - A morning in the life of Caitlin and James I wake up and it takes me a few minutes to remember where I am, I'm lying on my back in bed in a femininely decorated bedroom. I turn to my right and look at my beautiful boyfriend James, he's lying on his side facing me, his head resting on my shoulder, with my arm wrapped around him. I kiss him on the forehead, he stirs a little but stays asleep. He's wearing a pink...
I was bored at the house one day and nobody was home, or that’s what I thought. I was looking for some finger nail clippers and walked into my sister’s room and looked in her drawers. Well there I found a dildo. My sister is 18 and very beautiful. She’s got huge breasts and a super tight ass. I have thought about my sister in this really weird way before just because of times where we’ve been at the pool or the beach together and she would turn any guy on that looked at her.I picked up the...
CAITLIN AT THE BAT By Jezzi Belle Stewart (apologies to Earnest Lawrence Thayer) (c)2002 Turn Right Productions It looked extremely rocky at the Mudville home that day The score stood Casey zero; 'twas mom and sister's turn to play. For sister was fed up it seems with Casey's teasing game And mom was mad because it seems he treated her the same. Casey tried to plead his case in deep despair. At best He clung to the hope that springs eternal in each human breast; He thought perhaps...
"Please Master, I'll be quiet." "We'll see won't we?" Devon stood back, she looked so beautiful bound by the black restraints that contrasted silver shinny nipple clamps. He had already humiliated her, now he would work on self-control. "I want you to tell me exactly how you feel. We will do several things this afternoon and if I feel you are lying or hiding anything you will be punished. Do you understand?" "Yes Master." "Okay, tell me how you felt when you heard the first...
Devon showered and dressed preparing to meet his dinner guest. He would be lying if he said he wasn't nervous. Benjamin Kirkpatrick was one of the wealthiest most influential men he'd ever met. He came from old money but he had tripled their net worth in a matter of ten years. Their jewelry business catered to the rich, designing custom pieces for those who could afford them. Caitlin's diamond collar was a "Kirkpatrick". Concerned about the rumors he'd heard regarding Ben's temper,...
Caitlin laid back motionless waiting for Gavin to make his move. He appeared more nervous walking towards her than he did while being inspected by Devon. His large muscular body hovered over her as she lay, bound to the couch. Straddling her, he kissed her forehead then her nose and chin working his way down not touching her with the rest of his body. Taking the tab to her zipper between his teeth he slid it down her belly, his nose brushing between the soft flesh of her breasts now pouring...
I slid the report into the proper file just as he walked into the room. Dennis Butz stood there wearing his three-piece suit, looking as handsome and charming as any man could. But I was not to be tamed by his charm. "Hello, Linda," he said with a friendly grin. "Judge Herns isn't in today," I replied back in a frosty tone. "I'm not here to see her." "My plane leaves in less then an hour Dennis, what do you want?" I slammed the file drawer shut and walked past him to my desk...
“Hello! Anybody home?” Rachel shouted loudly as she pounded on the door to her home. It wasn’t her home actually it was her parents home, Rachel had just forgotten to put her keys in her purse before she took off to her class. She pounded on the door again getting frustrated. Finally after what seemed like hours she heard someone run to the door and unlock it.“I’m sorry it took so long, I just got out of the shower.” Rachel’s half brother Daniel said as he hurried to open the door for her.She...
IncestGood karma comes to Rachel on her friends' honeymoon.“On behalf of my wife and myself…” It was a traditional opening gambit for a groom’s wedding speech and it caused everyone, Rachel included, to laugh and applaud. Reece could carry off even the corniest of lines with grace and charm. “I’d like to thank you all for being here to celebrate our special day,” he said, concluding the sentiment and drawing out another appreciative murmur. American and Brit guests alike were loving him, especially...
Rachel sat sobbing on her front stoop. She couldn’t believe that her boyfriend had broken up with her. It was him that wanted to try new things. It was not her idea. What was she supposed to do?Rachel thought about her life and what led up to this point. She thought about when she was sixteen years old and going on her first real date. She thought about when she was eighteen years old and having sex for the first time. She thought about the boys and the things they wanted to do with her. She...
LesbianWith her three young daughters tucked up in bed Rachel sat watching the TV and, for the first time, she had chance to reflect on what had happened to her that day. She’d cheated on her husband and she knew that today’s huge events for her were going to change her life. She’d been married for fifteen happy years to Trevor and, despite him being away abroad for long periods, if she was feeling horny while he was away she would masturbate but it didn’t really solve the problem. She had never...
Rachel Rosenbaum bent over and lifted a box of oranges. G-d, they were heavy she thought, as her muscles strained to bear the weight. Her arms weren't used to this kind of work, as she had worked at a clothing store before her job here at a massive supermarket. It wasn't her choice to leave her old job, it was just that it paid better, and money was very important to her right now. As an 18 year old high school senior, she had to think about her future, which meant enough money for a state...
Rick knew that his sexy target often worked late, and all alone, at her fancy London office, so he set up a private meeting with the unsuspecting beauty. Rachel, you see, could never resist a tall, well-built Latino ladies man. She’d met Rick at an upscale dance club the weekend before. It was a setup. He kissed her, touched her, and teased her on the dance floor, whispering sexy words in her ear and making sure she felt the rock-solid bulge at the front of his tight jeans. Rachel was dazzled....
Pop pop popThe heavy bag moved significantly. The man striking the blows was Brad Johnson. At 43, he had an impressive physique. He stood no shorter than 6’3” and weighed in at 205. With 5% bodyfat, his well defined six pack and muscles left little to the imagination regarding the physical power he possessed. He had a long day at the office, as he is head sales manager for the Katsuragi corp. regional office in LA.His second most favorite way to relieve stress, especially after a long day’s...
CuckoldRachel graduated from the University of Oregon’s School of Law in May 1979 and, while studying for her bar examination in the fall, accepted a summer internship working for the regional branch of a federal agency housed in the eighteen-story Edith Green-Wendell Wyatt Federal Building in downtown Portland. Since her parents lived in nearby Lake Oswego, she could live rent-free while the internship brought in some extra cash to help pay down her student loans.Another benefit of the internship in...
VoyeurThis is a true story. “But MOM!” I pleaded. “I don’t NEED a babysitter! Can’t I just stay by myself this once?” But she wasn’t budging. For Pete’s sake, I was f******n. Just because my parents had to go out of town for the weekend, why did I have to have somebody staying with me like I was some little k**! “Look Jeff, I’ve heard all I’m going to hear from you. I’m getting Mrs. Walker’s daughter, Rachel to stay with you, and that’s all there is to it.” Then her voice softened somewhat. “Listen...
Rachel, My Naughty Little Tomboy Neighbor (Part one) The Orchard I heard giggling but there wasn’t anyone in sight. Supposing I had imagined the sound, I ignored it and went back to eating my apple. I was sitting on the ground with my back comfortably resting against a huge apple tree. It was my neighbor’s orchard I had invaded to ‘steal’ some of their succulent fruit. Of course now, I wasn’t really stealing. I’d been given explicit permission to pick some apples from the...
One of the young ladies I dated for a couple of years was named Rachel. She was 5’7”, 118 pounds, 34C-20-32. She had very long brown hair that reached the crack of her ass. Her eyes were brown and her face was quite pretty. Rachel looked like a fashion model and I enjoyed the way all of the guys watched her when she walked by. In fact, a number of ladies also watched her. All of this attention made Rachel very self-conscious as she did not like to be the center of attention. She preferred to be...
This story introduces us to Rachel and a sumptuous stranger. Thanks for comments and the inspiration. Kisses and Hugs.“How does this dress look”, it is the sweet voice of a female who is standing nearby. Rachel turns away from the dressing room mirror and looks at the speaker and the dress she is wearing. Rachel politely says, “That looks nice on you.” Jokingly she adds, “The bare feet add a special touch to the sun dress.” The stranger pulls up the dress and shows off her luscious legs...