Dating Kelly Part VI Spring Break Part 2
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I am 25 years old, married, and completely in love with my wife. We have a baby on the way, and this is the first of a series of true stories about our teenage years together, starting with when I first asked her out. If you're just looking for sex, you won't find it yet, not for a few more parts. When I was 16 years old I lost my virginity. I was always pretty shy, despite my ability on the athletic fields of high school, and the musculature that resulted from being a quarterback, wrestler,...
Love Stories"Oh fuck fuck yeah baby yeah Kelly ride my big dick. Let me stretch that tight pussy!" I was on my back and my girlfriend Kelly was sitting on top of me in the cowgirl position, bouncing around, causing her big tits to jiggle. Her blue eyes were closed and her mouth slack with ecstasy as her tight wet pussy was stretched open by my rock hard 9 inches. "Oh fuck babe I'm gonna-" With a start I woke up, laying in my bed, naked as usual, as my cock spasmed and sprayed my chest with cum. "Damn." It...
Love StoriesTwo weeks after I finally asked Kelly to homecoming, we had the dance. During the time between the two, I started hanging with Kelly more and more. We'd walk to school and back home together, she'd sit at my table at lunch, we'd sit on her front porch swing and talk for hours about ourselves. She was finally getting me out of my shell, but I'd still get goosebumps when she would hold my hand, or kiss my cheek. At the end of each segment of time I spent with her, she'd say, "Bye JJ, I can't wait...
Love StoriesAbout 2 months after the dance my parents went out of town for the week, taking my younger twin brothers and little sister with them. Since I didn’t have off school like my siblings did, my parents decided to let me stay home alone. After warning me that the neighbors were watching to make sure I didn't have any parties, they left. I was kind of laid up, because during the state semifinals football game, some defensive end on the other team got in a dirty hit. He got a "roughing the passer",...
Love StoriesThe Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Kelly deals with the fallout from the school article. Chapter 8 The first few days after the publication of Kirsten's article in the school newspaper, brought heightened focus on Kelly again. For the most part, the students that she spoke to were curious and politely asked her follow up questions. There were a few students though, that...
Chapter 40 "Mom?" Kelly was startled to find Marie sitting on Kelly's bed as Kelly entered back into her bedroom from the bathroom she shared with her sister. "What are... is something wrong?" "No honey, nothing is wrong." Marie smiled over at the girl wrapped in the towel. Holding out a shopping bag toward Kelly. "I just wanted to give you this before you got dressed for school." "What's this?" Kelly looked at the shopping bag in Marie's hands. "New bras honey." "But, I...
Chapter 24 Ed and Sabella had sat to watch the evening news before going off to bed so they could get back to their daughter Helen, who was still in intensive care at the hospital. The doctors had told them that they should amputate the leg, but Sabella refused to listen. This was her daughter, her own flesh and blood they wanted to do that to. Her husband had been more practical telling the doctors to do what they must to save her life before dragging his wife out of the room. To...
It was the fall of 1982. Kelly, who was now twenty-two, had recently started working for a new company. The thing she thought was a little odd about this new company, was that on any given day maybe half of the women in the office were braless. And it wasn’t hard to tell. Hard nipples. Big boobs swaying. It seemed like everyone had big boobs?Occasionally someone would wear something sheer. She had already clearly seen three sets of areolae in her short time working there. Boobs seemed to be a...
Office SexKeda My head was spinning; I just watched my young receptionist strip naked and masturbate. I worked for a small construction company. During one of our growth spurts we hired a new receptionist. Her name was Kelly. She was 19 and had just graduated from a tech school. She was beautiful, just loosing her baby fat and turning into a stunning young lady. She was about 5 feet 6 inches tall. She had the shiniest brown hair. Whitest perfect teeth. Great smile. Full lush lips. She had been a...
The Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Part 6 - This is the Sequel to Jason's Story. Chapters 15-26. The continuing story of Kelly Anderson, a young transgendered teen, as she faces the challenges with her mostly supportive family and friends. Author's Note: My sincere thanks to Joni W for all her efforts! Chapter 15 Kelly handed a box up to John, who was in the moving truck with Meghan's father. She looked back at...
Copyright 1999, 2002 by Wanda Cunningham. Lainie, Vickie, Rebel, Bashful, and everyone else thanks for the encouragement. There is no actual sex or transformation in this chapter, but I guess it should be rated R for context. So, nobody under 18 should read this, or whatever is the appropriate age in their community. This story deals with transgenderism in children and may be uncomfortable for some readers. Kelly Girl Chapter 13: "Another Hole in My Head" By Wanda Cunningham Kelly...
Criss 'n Kelly Part 5- A New Venture By Old Timer Kelly and I finally decided that our time together was more important than any outside activities such as driving a racecar. On the other hand, we both enjoyed being a part of it and decided to form the Earhart/Martin team using her present employees for race prep and support. What we needed was a driver and our next adventure was to find the right one. We figured we needed some eye sucking outfits so Renee made me a special...
The Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Part 1 - This is the Sequel to Jason's Story. A few months have passed, and Kelly is celebrating Thanksgiving. Author's Note: My sincere thanks to Joni W for all her efforts! Chapter 1 It was Thanksgiving Day, a fine autumn morning in late November. Kelly Anderson woke up and lay in bed thinking about all that she had to be thankful for. Her leg was finally healed and out of the cast. She had...
It was on a Monday late in September of 1983 when Kelly got the word that a customer would be in the office on Thursday. A customer coming to their office was not a common occurrence and only happened perhaps a couple of times each year. They always made everyone aware of it because there was a different dress code for those days. The most important part was that the ladies were expected to wear undergarments and no see-through tops. Dressing up a tad was the rest of it.On Tuesday, late in the...
Office SexIt was early January of 1989…“It’s okay to feel them,” Kelly said. His large hand reached down and felt the front of her panties. He gently rubbed the satin material that was covered in lace. He was lightly stroking her pubic mound. It was enough for Kelly’s clit to be in the game, but it wasn’t what she wanted.She gently wrapped her arms around his large bicep. She carefully tugged his arm, trying to get him to move his hand lower, onto her cunt. “They’re crotchless for a reason,” she...
ExhibitionismIt was Friday, July 4, 1997. Kelly and I had been invited to a surprise fortieth birthday party for a friend of ours. Cliff’s wife Shelly had been planning the party for several weeks and it was quite a shindig. Shelly had a great spread catered in. A co-worker of Cliff’s moonlighted as a bartender and he volunteered to bartend.With a bartender, most of the twenty or so invitees were drinking his delicious (and strong) concoctions instead of slamming cans of beer. The net of it was that...
Group SexThe Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Part 5 - This is the Sequel to Jason's Story. Kelly meets other TG Teens and the recession comes to town. Author's Note: My sincere thanks to Joni W for all her efforts! Also, thanks to JenniferBrock and Scott Ramsey for some plot advice! Chapter 12 Kelly looked out the window of the car, as she and her mother made the drive to...
That Monday Kelly was tied to her desk most of the day (I guess, considering this workplace, I should explain that she wasn’t literally tied to the desk!). Later in the afternoon she got up and was moving around on various errands. She unbuttoned a couple of buttons of her blouse leaving only three holding the shirt closed. She lingered at several desks. They all noticed her new nipple jewelry. Four guys felt her up that afternoon. Sandy asked her, “What’s up with you today?”“I don’t know; I’m...
Office SexIt was the end of August 1981. It was time for Kelly to move back to Milwaukee to take on her senior year of college. I was still out of town stuck working on a large project. Her brother Steve and his buddies had helped her load up her rental truck on Thursday. Steve had offered to go with her on Friday, to unload the truck but, with a wink, she assured him she would have no trouble finding help.Kelly was wearing a romper she had modified to fit her. She was a Small on the bottom and an Extra...
College SexCris 'n Kelly - Part 2 - The Awakening ? by: Old Timer I awoke alone in the bed feeling a bit sick and thought I had the flu or a mild hangover. Figuring Kelly would have some over the counter remedy, I went through my normal morning routine. With my light colored hair and mild beard, I can often skip shaving and this day was no exception. There appeared to be a fresh pair of Lady Jockeys that I put on as well as a clean bright green sleek running warmups with a side zipper. The...
It was around noon on Saturday when Deb woke me up. I didn’t see Kelly or Jack. Deb and I scrounged for some food. I found out that she was thirty-seven years old and that Jack was forty-eight. Deb could have passed for ten-years-younger without question. I came up behind Deb and she leaned onto the counter as I fucked her from behind. I brought her to orgasm and then dumped a load into her. It felt so great to cum a nice decent size load. She turned around and we embraced and kissed. Deb's...
Office SexCris 'n Kelly - Part 3 - Acceptance By Old Timer When I awoke, I was alone in her bed. Grabbing a towel, I hurriedly wrapped it around under my armpits as Kelly had suggested and headed to my room for a morning freshening. As I looked in the mirror, I was amazed that I still did not need a shave. If anything, my facial hair resembled blonde peach fuzz; and there was a softness to the texture as my splashed water and washed. No big deal I thought to myself, I never enjoyed...
Tuesday morning Tom, HR director called Kelly into his office. They had some polite small talk for a few minutes. Then Tom asked Kelly if she would please close and lock his office door. Kelly sat back down and said, “What’s up Tom?”“Mr. Johnson wanted me to let you know that he continues to be very impressed by both your work and your enthusiasm toward the company. He asked me to let you know you will be getting a $1,000 raise beginning with the next pay period.”“Wonderful!” Kelly said while...
Office SexWe untied and made the no-wake trip down river onto the big lake. Kelly was sitting out on the bow while Scott and I were cracking open cold ones on the aft deck. Once we were on the lake proper, Barry suggested to Kelly that she come back to the deck. Once she had a seat, he opened it up.Wow! Loud as all hell and fast! Hard to imagine something that big accelerating so quickly. We were quite a way offshore and had been barreling down the lake for maybe a half an hour when Barry slowed it down...
ExhibitionismWe untied and made the no-wake trip down river onto the big lake. Kelly was sitting out on the bow while Scott and I were cracking open cold ones on the aft deck. Once we were on the lake proper, Barry suggested to Kelly that she come back to the deck. Once she had a seat, he opened it up.Wow! Loud as all hell and fast! Hard to imagine something that big accelerating so quickly. We were quite a way offshore and had been barreling down the lake for maybe a half an hour when Barry slowed it down...
ExhibitionismIntroduction: Kelly gets more than she bargained for when she tries to seduce her ex girlfriends sister! Revenge is sweet, but pussy is sweeter Kellys Awakening Part 3 Id recommend reading the first two instalments of this series to fully understand the story, but, if you just want to read this one, or if youre a returning reader to the series, here is a very quick recap of what happened in the last chapter. Enjoy! P.T Jennifer has ended the relationship between herself and Kelly. Jennifer...
It was the end of January 1989. I had been out of town the weekend a few weeks previous. Kelly had spent much of that weekend with our close friends Patrick and Yvonne. They had a wild sex-fueled Saturday, the stories of which no one shared with me. Kelly just left it as, of course, the three of them had sex. It would have been odd had they not (which was true), and that was that.Yvonne called Kelly early in the week and told her that Patrick had received all of his prints back from the photo...
Group SexThe Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Part 2 - The continuing story of Kelly Anderson, a young transgendered girl and the trials and tribulations of life, with her mostly supportive family. This is the sequel to Jason's Story. Author's Note: My sincere thanks to Joni W for all her efforts! Chapter 4 "Mommy, when are we going to see Grandma and Grandpa Anderson again?" Billy asked. "I don't know, Billy." "I miss them. I...
Stephanie opened her eyes slowly. She had a disoriented look on her face. When she saw Kelly's wet face it all came back to her. A weak smile crossed her lips. "Your face is all sticky," she whispered. "I know," Kelly answered and licked her lips. This time, Stephanie pulled Kelly's lips to hers for a very wet kiss. When she pulled back, she stared into Kelly's eyes with a look of concern on her face. Kelly knew what she was thinking. "You don't have to do that to me," she...
Introduction: Kelly learns everything, and it isnt all good Kellys Awakening Part Four Once again, as with the previous parts, Id recommend reading the first few stories so that this one makes more sense to you! For those of you that just want to read one story, or if youre returning to this series, heres a quick recap from the last story. Enjoy! [After seven months Jennifer, Kellys girlfriend, had ended their relationship because she suspected that Kelly desired her sisters, Amy and Bianca,...
It was July 1990. Kelly and I had returned from our weeklong trip to Spain barely two weeks before. In that time, Kelly’s pussy was on fire! She was still wildly turned on by our adventures in Spain from gang fucking on the beach to being groped and jerked off in the pub. All of it had her wanting nothing more than to orgasm at every chance she could get.She would wake up in the early hours of the morning and feel for my cock. If it was hard she’d roll me onto my back and climb on top, slipping...
ExhibitionismIt was July 1990. Kelly and I had returned from our weeklong trip to Spain barely two weeks before. In that time, Kelly’s pussy was on fire! She was still wildly turned on by our adventures in Spain from gang fucking on the beach to being groped and jerked off in the pub. All of it had her wanting nothing more than to orgasm at every chance she could get.She would wake up in the early hours of the morning and feel for my cock. If it was hard she’d roll me onto my back and climb on top, slipping...
ExhibitionismIt was December of 1982. Kelly wore a white sheer top and a rah-rah mini-skirt to work on a Monday. She left her bra and panties at home. She received appreciative looks--no, stares--from all of the men. Each, at some point during the day, made a point to stand before her and study her tits with various degrees of subtlety. Kelly was positive that by the end of the day none of them knew that she has blue eyes. Kelly, being Kelly, really struggled that whole day with keeping her shirt on. It was...
Office SexKelly, Tricia, Alan and I headed to the larger city down the highway. It was a half-hour or so and they had a Shopping Mall, which was a big thing in 1980. The mall was actually quite busy with folks making returns and whatever. Both of the girls were wearing flannel shirts and Levis. Pretty normal compared to everybody. Along the way, I had been copping some feels and knew that neither girl was wearing a bra. Kelly knew how to walk to suppress the jiggle, just as she knew how to walk to...
Group SexAfter Vinny had cum all over her panties, Kelly decided that she didn't really need to wear them anymore. Kelly came back into the room completely naked. Even though he was tired, Vinny was interested in seeing her nude body up close."Kelly, come over here and lay down on the couch for a minute," Vinny said. "I just want to look at you real close.""Whatever, but I get to do you next," she said laughing.Kelly laid down and started to watch TV although she was excited by having her brother this...
A couple of months had gone by and Becky and Kelly had become good friends. Not really talking about sex all the time, but it had been mentioned a few times. Becky and Steve were not getting along during this time. His work was on a slow down and his hours were cut and since Becky did not work, bills around the house started to get out of control and they would have some heated arguments over their finances. Steve was the type that didn't want his wife working and thought her place was at...
About that time, Kelly and Marcus came up to us. Marcus was as hard as a rock and Kelly said “Well, we are heading back upstairs. Have fun you two. I know we will!” They left and I was about ready to take Becky upstairs too. Before I had a chance to, Becky said “Can I please have a glass of wine?” I told her sure and we walked in the kitchen to get it for her. She said she was a little tipsy from the daiquiris, but wanted some wine to mellow her out. I said “Don’t get so hammered that...
‘Oh fuck fuck yeah baby yeah Kelly ride my big dick. Let me stretch that tight pussy!’ I was on my back and my girlfriend Kelly was sitting on top of me in the cowgirl position, bouncing around, causing her big tits to jiggle. Her blue eyes were closed and her mouth slack with ecstasy as her tight wet pussy was stretched open by my rock hard 9 inches. ‘Oh fuck babe I’m gonna-‘ With a start I woke up, laying in my bed, naked as usual, as my cock spasmed and sprayed my chest with cum. ‘Damn.’
Cris 'n Kelly - Part 1 - The Beginning ? by: Old Timer My introduction to the driver known on the race circuit as 'The Eradicator' was short, but definitely not sweet. It was during the 'happy hour' practice session when everyone's out there trying to sort out the setup and make those little tweaks for race day. I thought I was driving smoothly with pretty good pace and following the line while watching my mirror for any approaching problems. Out of nowhere, I felt a slight...
Becky looked over toward the Jacuzzi and through the gazebo, she seen Kelly kissing Marcus and said "Oh my God! Look at them two." I looked over and Marcus was sitting at the Jacuzzi and Kelly was in the water facing him and they were kissing. I joked and said "Marcus is just saying thank you for dinner." We both laughed and as Becky leaned to grab the bottle of wine to refill our glasses, she scooted closer to me. Becky told me that one time, she went to a bachelorette party and they...
I asked Becky to hand me the bottle of warming oil and when she did, I squirted it just above her cunt. I handed it back to her and started to rub it in. I used the lubrication on my fingers to rub it on the opening to her cunt too. Then, I leaned down and started kissing her cunt and started to blow on it. This drove her crazy and she was wiggling underneath me. Becky said “Lay back for a minute.” When I did, she sat up and poured a bunch of the oil in her hands. Using both hands, she...
Kelly Takes Control Part 1: The Decorator. A work of transgender fiction, contains depictions of sex and black mail, if you are offended or too young, do not read on. *** Kelly opened the door to their home. She took a deep breath "he'll be looking at porn again" she thought grimly. "Am I not enough for him? I really can't understand why he looks at all those other women, all those sluts! Chin up, tits out, you can do this'. Kelly pushed open the door, home slightly earlier...
Saturday morning came early for the younger Bundy f****y members, Buck as usual was humping Marcy’s poodle, Bud had just screwed Amber and she was staggering back to her aunt’s house butt naked and tired, Bud has now crawled back into bed to cuddle up with his other warm piece of ass for the morning, he had started out fucking her, but duties called for him to service Amber and to keep her pussy happy. Kelly sl**ps soundly as usual as she normally gets back home around 2am from one of her boy...
Saturday morning came early for the younger Bundy family members; Buck asusual was humping Marcy's poodle; Bud had just screwed Amber and she wasstaggering back to her aunt's house butt naked and tired; Bud has nowcrawledback into bed to cuddle up with his other warm piece of ass for themorning,he had started out fucking her, but duties called for him to service Amberand to keep her pussy happy.Kelly sleeps soundly as usual as she normally gets back home around 2amfromone of her boy friends,...
Kelly and Becky were both wearing the babydolls they bought earlier. Edward and Marcus started to remove Kellys and Norris and I started removing Beckys. Once both were undressed, Edward looked at Kellys bare cunt and then at Beckys bare cunt and remarked “Holy shit! Nothing to catch the jizz as it leaks out! You are going to let me fill that sweet pussy aren’t you?” Little did he know that Kelly wouldn’t need hair to catch anything and Becky was just a small dribbler! (at least so far) Kelly...
The Life and Times of Kelly Anderson Written by Kristine Roland Edited by Joni W Part 3 - This is the Sequel to Jason's Story. Author's Note: My sincere thanks to Joni W for all her efforts! Chapter 7 Kirsten came over to the lunch table where Kelly and her friends were sitting. She was carrying a stack of papers. "Kelly, here you go, hot off the press, the new edition of the Jefferson Weekly," Kirsten said. She handed a copy to each of them and gave a handful to...
If you missed the first part, go find it - Back in College with Kelly.I came home from class one early afternoon to find that Kelly left something in my room for me. She always had a key to my room so she could enter the building and get up the elevator and so I didn't have to go get her. On my bed was a bag from the local clothing store in town. There was a note that said, “Put this on and wait for me. I’ll be back later. Love, Kelly.” When I opened the bag, I instantly smelled her perfume and...
It was Memorial Day weekend of 1998. Kelly and I were thirty-eight and had recently bought a small motorhome. We were camping at a state park, which we preferred as the sites were more spacious and had more trees than what we’d found at private campgrounds.Friday evening was absolutely beautiful. Kelly and I sat at our small campfire until after midnight just enjoying each other’s company and being outdoors. By the time we went to bed we were exhausted. Even so, we both slept naked, just to...
ThreesomesThey laid there for several minutes. Jason then asked if he should go home and Kelly said "Why? Are we done already? I don't know about you, but I'm just taking a break!" Jason said he would stay as long as it was okay. Kelly said "Then I want you to stay!" Kelly suggested that we go downstairs and grab something to drink and relax for a little bit and then come back upstairs. When Kelly climbed off the bed and stood up, just a little bit of cum leaked out. Instead of asking for a...
Peter sat by the table on the terrace of his house fixing his glasses with some tape. Everyone in his life had told him to buy new ones, but he refused. The glasses were the same he had used back in college to edit his first porn video and he felt they were the reason for his success, his lucky charm. He had changed the glass a few times over the years as his eyesight changed. Checking that the frame held together, he cleaned them and put them on.“Honey, why don’t you come in?” the voice was...
IncestShe even had a semblance of curves. Beneath Kevin's baggy clothes, hidden, was a delicious figure. Kelly stood in front of me, beaming down at me. She shifted her weight onto one of her hips, and placed her hands at her sides. "So? How do I look?" I couldn’t begin to describe. I could still see Kevin in there, but there was more. For me, there was a woman standing in front of me. She was a little boyish in figure, but she was smooth, curvaceous, and projected an aura of powerful...
We walked into the bedroom and Kelly removed the bedspread to expose the new dark blue satin sheets and pillow cases she put on the bed earlier. I plugged the camera in so the batteries wouldn’t go dead in the middle of any good part and I put a new tape in just in case I needed more then what was left on the first tape. Jason said “Uhh. Will I need a condom? I didn’t bring any.” Kelly said he wouldn’t need them. Jason said “Good. So you are on the pill?” Kelly looked at Jason and gave...
Rated R for context. Nobody under 18 should read this, or whatever is the appropriate age in their community. This story deals with transgenderism in children and may be uncomfortable for some readers. Kelly Girl Chapter 14 "Floop and Happenstance" By Wanda Cunningham Kelly stared, squinting a little without his glasses. Andie had just removed Melissa's wig revealing thinning brown hair and a receding hairline, very much at odds with the rest of Melissa's appearance. Moments before,...
Oola was the black woman whose tits Kelly was so fascinated with at her first company orgy. Oola worked in customer support at the far end of the building from Kelly. Once in a great while, Kelly would need to go see her about something in person. One day she had heard Oola was wearing a see-through blouse. Kelly had to see her tits again so she made up some excuse to go see her. She sat in her cubicle talking about whatever it was. She couldn’t take her eyes off of her boobs. Oola unbuttoned a...
Office SexI was laying next to Becky and she said “So now what?” I joked and said “Now… we go to sleep!” She gave me an odd look and I told her I was just k**ding. Then I said “Now, we have to talk about this just good thing!” Becky said “I’m so sorry. I meant it was great and not just good. I didn’t mean to say that.” I told her that she already said it and now, I have to make up for it, and said I have a reputation to uphold and I can’t have anyone thinking I am only good. I put my hand over...
Kelly finally caught up to the present and slowly rolled off of Jason and turned around. Once again, on her side, she was facing him and had her upper body over his, she was staring right into his eyes and neither of them spoke for about two minutes. Kelly leaned in and kissed him on the nose and said “You made me see stars! That was earth shattering! You just wait until we are rested. I am tearing you up tonight!” Before Jason had any chance to say anything, Kelly leaned in and started...
Cris n' Kelly - Part 4 - More changes By Old Timer The next several weeks were spent learning how to dress appropriately. Kelly tutored me on the basics of makeup and hair styling while encouraging as she noted my successes. My inner female must've been stimulated because I rapidly gained confidence in these daily tasks and could easily accomplish an adequate 'look' in the same time as if I were shaving. We also enjoyed getting manicures though I insisted on a simple clear...
"We can meet at Peter's Pub. It's not far from my place on Rosewood Lane." "Okay, I'm sure I can make it," Stephanie said, deciding to call a babysitter if her mother wasn't available. The following Friday, Stephanie drove to the pub to meet Kelly. When she entered, she looked around in the dark restaurant and saw Kelly sitting in a back booth waving her hand. Then with a bright smile, she made her way to the booth and slid in across from Kelly. "No problem finding the place...