Doing Debbie
- 2 years ago
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It didn't happen the first time. I'd wanted to take Debbie out but she'd said her father didn't want her to go on the date because he thought she was too young. Some years later, I found out by asking Debbie directly that the reason she didn't go on the date with me was because she was too shy. Ah, what a loss for both me and Debbie, but sometimes in life we have a chance to do things that we messed up the first time. Going out with Debbie was one such experience.
I asked Debbie out because I thought she was one of the cutest and nicest girls at school. She was a freshman and I was a junior and I wanted to spend the entire evening with her. She was shy and I'd dredged up enough courage to ask her out only to have her say "No". Because she'd turned down the invitation, I asked another girl out and had a great time, but I hadn't gotten over my infatuation with Debbie. After some years, I still had a very special place in my heart for Debbie and I got a second time to enjoy spending an evening with her.
When I'd first asked Debbie out for a date, she'd been a typical shy young teenage girl who had never dated and who was scared to death of going out with a boy that she found attractive and interesting. I was crushed. I really wanted to date her, but when she didn't take me up on the offer, I did manage to get another very pretty and very fun girl to go with me. But, there was always that desire to have spent time with Debbie. When she was a young teenager, Debbie was very cute and had an obviously budding set of nice breasts, a very trim and shapely figure and a winning personality although she was very shy and quiet.
When I met Debbie several years later, she was now an adult woman, had been married and divorced and had given birth to two children. That put Debbie squarely in the category of "mommy pussy" and made her even more attractive to me than when she'd been a shy, virginal young teenager. I wanted her back then; I wanted her even more now as a young adult.
When I saw Debbie again, I instantly recognized her -- she'd only grown more attractive -- and found her as sexy as ever. A few years of maturing, having two children, and the normal sexiness that a woman picks up as she becomes a real woman had all added to make Debbie much hotter. When I'd thought about Debbie over the years, I often wondered what that "missed date" would have been like. I'd fantasized and imagined it many times.
I had never actually expected to see Debbie again -- but when I did my mind began churning to see what I could manage to make happen. Finally, I just decided to try what I'd tried several years earlier -- ask Debbie out on a date and see if this time she'd agree. We'd call it" going out for dinner" but the result would be the same -- time alone with Debbie.
When Debbie and I met at the restaurant, we both immediately moved towards each other and hugged and I knew that there had been much much more between me and Debbie from the feel of that hug than I'd ever hoped could be true on her end. She hugged me close and I resisted the temptation to do anything naughty, but finally after too many years, I was feeling Debbie's womanly body in my arms, and I loved the feel of her nicely rounded B-cup breasts firmly pressed against my chest.
The dinner was like something out of a Hollywood film. Here were two people who'd made some crucial mistakes in their past and had almost missed ever being with each other. As we sat there eating and talking quietly, I finally said some very pointed and honest things and I could see tears begin to form in the corners of Debbie's eyes and then they started to stream down over her smooth beautiful cheeks.
"What?? Did I say something wrong, Debbie?" I asked, not wanting to hurt her in any way.
"Oh no, Tom. You didn't hurt me at all. It just suddenly struck me how much I'd loved you for so many years and how silly I was that night to tell you that I couldn't go out on a date with you. I cried for hours that night, knowing that by telling you that I had probably lost you forever. And I had. Tom, is there any way I can make it up to you for the lie I told you that night and for not being honest with either of us?? Can I do anything to make something out of a very bad decision that I made as a shy introverted young teenage girl?"
"Yes, there is, Debbie. There's one thing that I would love for you to do -- would you let me make love to you?"
"Oh, Tom, if you were any other man in the whole world, I'd be offended by your question and I'd probably smack your face right now and get up and walk out. But, you, Tom, if you'd asked me any other question but that one, I'd have been so disappointed. I'd have been so crushed that you didn't want to make love to me. Oh yes, Tom, oh yes, I would so much love for you to me tonight, Tom, more than anything I can think of. Oh yes, Tom, please take me and make love to me."
Debbie pulled into the parking lot at her work place.Traffic was horrible this morning, she thought to herself as she checked out her reflection in the mirror.Debbie is 27, 5'6, 110 pounds, with long red hair, sparkling blue-green eyes, and 34c breasts.She lives in New York. She opens the door of her 2000 Black Ford Mustang and steps out onto the pavement, taking a deep breath.Debbie walks up the step and into her office building. She waves to her coworkers and goes to her desk. She sits down...
Janet and Debbie were sitting home on a Saturday afternoon, just lounging around, naked as usual without any plans for that night. Suddenly, Janet had an idea. She asked Debbie if she would like to participate with her in a gangbang with just black men and maybe a black woman or two. Debbie told her that she had never fucked any black men or women and that the idea sounded wonderful and if that was what Janet wanted to do, she would love to do it with her and fuck her first black man. Janet...
Robert and Debbie are your average Americans. Working and struggling to live a good life in America. They have been married for twenty years. Debbie is now in her middle forties but you would never know that from her pictures. She has very large breasts that are plump and firm. Her waist still thin and tight. She is what they call today (thick). Thick like Kim Kardashian thick, although Debbie is a blonde. Debbie carries this very well. Debbie is 5'4" and 115 lbs. She has 36 Double D cups. She...
It was late at night, last fall. I was walking up to their house and my heart was pounding. The lights were on and I had already walked by the house once. 'Would I ring the bell?' The excitement was racing through my body and I had an erection that wouldn't stop. I would really regret not walking up there.I put my foot on the step of their porch, stood in front of the door and took a deep breath. Without thinking I pressed the doorbell. I couldn't back out now without fleeing in terror.I heard...
I’m going to tell you a very interesting story about a vacation we took with my wife’s father and his girlfriend. We went to Puerto Vallarta in Mexico. My father-in-law insisted on paying and wanted to treat us. My parents were kind enough to watch our children for the week. My wife and I haven't been on vacation without them in years. I was hoping to talk my wife, Jessica into being a little spontaneous on our vacation. Jessica sometimes could be very timid, when it comes to sex. I was going...
Group SexHi, my name is Don. My wife is Debbie who is thirty-five, blonde, blue eyesd and five feet tall. We've been married for seventeen years. We met in high school and have been sweethearts ever since. Both of us were virgins when we met, so you can appreciate that neither of us has had much sexual experience with other people. When we hold each other, the top of Debbie's head rests just under my chin. Sex is incredible, but sometimes having Debbie in my arms is better. There is nothing greater...
CuckoldHi, my name is Don. My wife is Debbie who is thirty-five, blonde, blue eyesd and five feet tall. We’ve been married for seventeen years. We met in high school and have been sweethearts ever since. Both of us were virgins when we met, so you can appreciate that neither of us has had much sexual experience with other people. When we hold each other, the top of Debbie’s head rests just under my chin. Sex is incredible, but sometimes having Debbie in my arms is better. There is nothing greater...
If you haven’t read Chapters 1 and 2 yet, I suggest you read them first to pick up details not included in this chapter. *** We woke up finally around 11:00AM and while I cleaned up I noticed some cum around my pussy lips. I thought I’d cleaned everything up last night, but either I failed to or else some cum oozed out of my pussy during the night and onto my lips. I was beginning to get worried-Tom had not pulled out in time and it was my fertile time of the month! We checked out of the...
We had moved to WA. Sue had promised me that she would not continue her cheating ways if I took her with me. We had been there less than three weeks and she was pushing me to allow her to break the promise. Marg was due in a few days. Sue had encouraged me to have sex with the babysitter. I was reluctant because she had only recently turned eighteen and I did not want to do anything that could cause her any harm or stress. I agreed only on the basis that she made all the moves. Sue and I were...
Group SexThis story happened about twenty-three years ago. Shortly after our daughter was born, our sex life shifted into high gear and we had great sex almost every night. Debbie had lost a lot of weight after the pregnancy, looked great and knew it. She started wearing more revealing clothes -- shorter shorts, halter-type tops, slinky sundresses and often went without a bra and sometimes, even without panties. She bought some very sexy teddies and nightgowns and we played in the evening for hours at a...
Joy took Debbie's hand and led her out of the room and down a hall. They entered a room that was filled with fancy clothes and lingerie. "You're pretty tall but I know we have something for you." She sorted through a rack until she found a strapless black silk dress. "Try this on for size," she said. Debbie held it up and saw that nothing would fit under the clinging material. "I don't have a body suit to wear under this." "It's too tight for what I'm wearing now." "Don't worry...
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SwingersIntroduction: The girls let Steve tape them skiing and dancing in their bikinis and show the tape to our friends. This story is partly fiction. Debbie did have a skimpy white bikini that showed her nipples, aureoles, cunt hair and cunt when it was wet. She liked everyone looking at her when it was wet, especially when she got into the boat and brought her rope in. Debbie loved being videoed and being seen naked. About two weeks after Steve moved to town, before he had fucked her my wife,...
It was the last Thursday night of the month and time for another session of Ten Questions. Bill and I were headed for our favorite campus watering hole to find this month's lucky contestants. We walked into 'The White Tiger Tavern' and headed for the bar. The place was not too crowded, but it was still early. We ordered a beer then leaned back to check out the babes. Several potential candidates entered the bar, but unfortunately all were with a date. We hit pay-dirt about twenty minutes...
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DISCLAIMER: All characters appearing in the series, ‘TOM & SUE JOHN & DEBBIE,’ are fictitious, as they do not exist. Any resemblance to a real person, living or dead, is purely coincidental, and should not be construed to associate a real person, living or dead, with the scenes or events described within the series ‘Tom & Sue John & Debbie.’ I hope you enjoy my story Reverse Cowgirl. * * * As I lay in bed relaxing, Tom was downstairs watching the NBA playoff games and I noticed the date,...
Introduction: Second part of a fictional story Educating Bobby And Debbie Part 2 Debbie and Diane Introduction: My fourteen year old son Bobby has been seeing a fourteen year old girl named Debbie, for the last few months. I had given them a good education on the real sex between two people that schools wont teach and all teens should learn, as they gave their virginity to each other. Last week my brother Larry invited my son Bobby to go to a Nascar racing weekend at the Texas motor...
Thinking back on my life brings back lots of memories, and the occasional fantasyabout "back then." I'm not dead yet, and some of you might find my talesinteresting. Check out the intro if you want more background. Living in thecountry was great fun, and it was becoming even more interesting.Jeff Zephyr's Life JZL10_01: "Playing Naked in the Wild - Debbie in the Woods" Age 10. (bg exhib, bbgg exhib, p*****n, no sex)It was about a month after school let out for the summer, not long after...
Part 2 Debbie and Diane Introduction: My fourteen year old son Bobby has been seeing a fourteen year old girl named Debbie, for the last few months. I had given them a good education on the real sex between two people that schools won't teach and all teens should learn, as they gave their virginity to each other. Last week my brother Larry invited my son Bobby to go to a Nascar racing weekend at the Texas motor speedway. They left on Thursday morning, and wouldn't be back until late...
If you haven’t read Chapter 1 yet, I suggest you read it first to pick up details not included in this chapter. The series, ‘Tom & Sue John & Debbie’ is about sex, sports, and romance as the fictitious characters take the readers on a roll coaster ride with each chapter building on the previous chapter. The story plot centers on the adventures of two HS senior girls who are best friends, but come from different social and economic families. One is a star basketball player from the poor side of...
About two weeks after Steve moved to town, before he had fucked her my wife, Debbie, bought herself a new bathing suit for sunbathing. Both the bottom and top were unlined. It was really skimpy, exposing an inch of the bottom of her tits, and two inches of the outsides and three inches insides of her tits. The top part went clear down to the edges of her aureoles. It was really soft and stretchy and molded perfectly to her tits and nipples, without distorting her nipples. The...
When Mike had finished at university, he was due to start work in his chosen profession with a top law firm working in the city. He had passed his law degree with a first and because of this, he had found that he had first pick of most of the positions being offered to graduates. He was going to spend his first year working as a trainee lawyer while Debbie would be finishing her degree at Warwick University. They were still very much in love with each other and had shared a flat during Mike's...
SpankingAs Debbie lowered herself onto Kevin’s cock she groaned loudly, her mind cast back to 2 days earlier when she had been riding a bigger and much thicker cock, Kevin held her hips as Debbie started to grind on his deep rooted dick, her mind now consumed with the cock she had been riding and sucking was really turning her on, she had met up with a few mates from work and had gone for a few drinks, getting chatted up by Jason she was unable to resist his cheek and ended up getting nailed into his...
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MatureFifty-five-year-old larger lady Debbie Simpson had had what she was now convinced was the fucking of her life when she hooked-up at the annual company conference with the considerably younger Simon Curtis.In the few weeks since that night of sex, she had had two sexual encounters of sorts but neither was particularly successful and certainly neither were satisfying for her.On the first one with a youth of eighteen, he ejaculated in his underpants before they really got started and he fled in...
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First TimeChapter ONE My fourteen year old son Bobby has been seeing a fourteen year old girl named Debbie, for the last few months. One night I was getting a light bulb from the closet in the hall outside his bedroom door. I heard Bobby and Debbie talking about trying sex, but they were both virgins, and didn't know how to begin or what to do. I knocked on his door and stepped in. I told them I had over heard their conversation. I told them I was not angry with the and they were not in any...
Debbie Does Me.As I was in the area I decided I’d call and see Debbie. She’s a good sort and always brings out the best in people.As I arrived Debbie was about to leave but said you can come along it just might make things more interesting. She said it would be fun and there seemed to be a glint in her eye as she said it. She was wearing a long black coat heels and red lipstick. She looked devilish and bemused by her I said ok to which she replied I hope you don’t shock easily with a definite ...
Big Al got out and opened the rear door of the unit and said, "Careful getting out Miss, don't want no bruises or cuts on those pretty legs." His manner gave Debbie the chills as she struggled to get out of the low back seat without the use of her arms. Big Al reached down and grabbed one arm and pulled her up to her feet. The touch of this man made Debbie feel soiled. They passed though many steel doors into a small room where she was told to sit down on a hard metal bench and be quiet...
How my wife was seduced and awakend sexually during a Labor Day cookout with our new neighbor. My wife and I have been married for going on 10 years now. We married shortly out of high school and had a pretty good life together for most parts. The only area we had any real differences in was sex. Debbie had a very low sex drive and two or three times a month of routine ordinary, nothing to wild, sex was sufficient for her. I on the other hand wanted to go several times a day and the wilder and...
EroticDear Readers, If you haven’t already read Chapters 1-8 of this series, Tom & Sue John & Debbie, I suggest you do so. Readers will follow the fictitious characters while they take the reader on a roller coaster ride filled with sex, sports, and romance. Each chapter builds on the previous chapter and without reading the previous chapters the reader will miss out on a lot of detail regarding the characters and the story plot. I hope you enjoy my series, ‘Tom & Sue John & Debbie.’ DISCLAIMER:...
As Debbie and I walked into the mall, I tried to convince myself that I looked perfectly normal. Just a teen cheerleader walking the mall in a bikini top and tight shorts. Maybe a little inappropriate, but not obscene. I tried but failed. Everyone was staring. People were pointing. I even heard one man say to his wife to, “Look at the naked little girl over there!” Little girl! He called me a little girl! Not a young lady. Not a teenager. A little girl. It was my biggest fear that my little...
Author's Name: Lee Anne Montgomery ([email protected]) Story Title: Woman Partner (Chapter 4, Debbie Introduces Me To Nightgowns) This work is copyrighted to the author © 2003. Please do not remove the author information or make any changes to this story. You may post freely to non-commercial "free" sites, or in the "free" area of commercial sites. Thank you for your consideration. I look forward to, and hope that I receive, your feedback....
Debbie was alone at a cozy, fashionable restaurant not far from her office. Lunch with a prospective client had gone beautifully. The client had signed where it counted, making a tidy profit for Debbie's insurance company. Though her face and body were only slightly different than they were before Paris, a trifle slimmer maybe, a bit more toned up, you would hardly recognize her as the same woman. Every eye, male or female, followed Debbie when she walked sexily into a room, and she only...
Debbie, Crane driver Debbie, Crane DriverSynopsisDebbie finds that getting to the top in a man's profession can be a difficult and painful experience. Debbie, Crane Driverby obohobo WarningsPlease take note!The text in this story contains erotic material and is expressly written for adults only. MF NC. SpankingIf you are underage or offended by such material, or if viewing this file is illegal in your locality, then leave, close or delete this file-story now. This is a work of fiction,...
Debbie and Barbie Do Reno by Debbie My wife Barbie has been very supportive of my need to dress up for all of the time we have been together. The day before she was to move in with me I told her of my desires. I guess it was my way of giving her a chance to back out. I didn't know what to expect. She said she had just seen a film about transvestites in one of her classes at college. She began to tell me about how the transvestites tucked their penis to get a more finished look....
I knocked softly on Nicky and Randi's door ten minutes later. I didn't want to wake the others. "Come in," I heard a female voice call out, so I eased open the door. The room was packed. I stopped and stared as I quickly took it all in. Nicky and Randi were there, along with Jenny, Julie, Grace, Candy, and Mandy. The surprise was finding Sarah and Debbie there as well. "Okay, I give," I told them without reading them. "What's going on?" It was Sarah who answered. "Michael, I...
Ann and Debbie had been living with me for a couple of months now with Debbie basically running the great sex life (see part 1 ) I now enjoyed. Her mom still didn't realize the pictures didn't exist so when Debbie told her to move she moved. As you learned Debbie wanted a sleep over for some "friends" of her's this weekend. Keep in mind Debbie is only 11 she will turn 12 in June 3 months away. I bought 2 sets of bunk beds for Debbie's room and moved the full size bed into the guest room...
When she phoned that first night Debbie told me that she had met two interstate men in the dining room who represented a variety goods company and had some excellent product that would suit our country business. I told Debbie to do an order with them, but she explained that she would rather I saw them myself as they were also looking for warehouse space in our state and there was maybe an opportunity to cash in on that. John and Tony called in about a week later, and their product was as...
MY STORY: My wife and I have been married for about five years, and while we are very monogamous, a recent event changed my mind about monogamous relationships. As an Army Officer I am expected to attend certain social events, and while my wife is not a social butterfly she goes along with me, because she knows the political importance of being the “prim and proper, socially connected” Officer’s wife. My Battalion Commander was throwing a Party at the “O” club (short for the Officer’s Club)...
Wife LoversIntroduction: Judy wants to bring her stuck up sister into the game At this point, Gail would do whatever Judy wanted her to do. For that matter, Gail would simply follow instructions of whoever was in charge, as long as it led to her total humiliation and sexual stimulation. Gail was worshiping Judys ass and reaming her puckered hole with her tongue like the good slut she was. This was getting Judy pretty worked up, but it wouldnt bring her to an orgasm. Judy abruptly turned over leaving Gail...
If you haven’t read Chapters 1 through 4 of this series, I suggest you start at the beginning. You’ll get more out of this story if you do. * * * * * * Sally asked, ‘Sue, did you and Tom use the ultra-thins every time you fucked this weekend?’ I said, ‘Yes. We both don’t want the worry ever again.’ Steve and John came back to the house so we quit our sister chat. John turned on the TV and the ESPN sports was on. He yelled, ‘They’re interviewing Coach Lewis at the Superdome.’ We all ran...
George was looking at my small breast and he bent down and started sucking on one then the other. God that felt so good. I bent my legs and placed the heels of my feet against my ass check and spread my legs as far as they would go. George took one of his free hands and spread my bald cunt lips apart exposing my hard little clit to the air. It stood attention when he started to rub it. I could feel my pussy getting wet. “Please fuck me some more.” I begged. George just raised his head from my...
This is a true story. My first three-way happened when my girlfriend, Diane and I were experimenting with our sexuality. She admitted to me that she found women attractive. In fact, when she was younger she had a brief lesbian affair with her cousin. I told her I found the thought of her and I having a sexual encounter with another woman highly erotic, and she agreed.We thought about whom we might find to have a three-way with. I asked her if she found any of her friends attractive.“Yeah,...
One Friday afternoon after everyone left work for the day, I thought, I called my wife to make plans for the evening. She had gotten off work early and was home alone and we started to have phone sex. My wife loves playing with her pussy and I love playing with my cock so, we get along great. Sometimes we have sex and cum together without even touching the other one, I guess you can say we love boing watched. Debbie the office manager had forgotten her phone at the office and had driven back...
Dear Readers, If you haven’t already read Chapters 1-7 of this series, I suggest you do so. Otherwise, you’re going to miss out on a lot of detail. The series, ‘Tom & Sue John & Debbie’ is about sex, sports, and romance as the fictitious characters take the readers on a roller coaster ride with each chapter building on the previous chapter. The story plot centers on the adventures of two high school girls who are best friends, but come from different social and economic families. One is a star...
Looking down at Gail, Judy said, we’re going to have some fun this weekend Gail. We’re both going to like it. We’re going to go to the Octoberfest in Flagstaff, you and me, my sister the bitch and of course our husbands. You’re going to fuck my sister’s husband and then you’re going to turn my sister into a cunt lapper, just like you. I’ll figure it all out, you just need to convince your husband to Flagstaff for the weekend. Tell him he’ll not only get to fuck my sister, but watch a girl...
We drove into the center of town and parked on Main Street in front of the tailor’s shop. “The tailor here is a friend of Ms. Connor,” Debbie said and opened her car door. I was still wearing the baseball cap and boy shorts with no top. I hesitated a moment, since there were people walking up and down the sidewalk. I took a deep breath and got out of the car. It was a short walk from the car to the shop door and I made it without anyone noticing that I wasn’t really a shirtless boy. Debbie...
Thank you for reading my series, ‘Tom & Sue John & Debbie.’ If you haven’t read the previous chapters 1-9, please do so before reading this chapter. Otherwise, you’re going to miss a lot of the details as each chapter builds on the previous chapter. Chapter 10, gives the readers a ‘hint’ as to what will happen to the fictitious characters as they continue to take the readers on a roller coaster ride filled with sports, romance, and sex. I hope you enjoy the series and I appreciate your votes...
Debbie wasn’t the best looking girl in the office. In fact, the waste bin looked more attractive. But there was something about her that I couldn’t put my finger on.She was hard working. She often stayed behind when everyone else left. Never did I have to chase her up over a project. Her dead lines were always met easily.In truth, she was about five, five, red hair, and dressed in loose fitting clothes. I guess this was what made her look so different from the other office girls.Her make up was...
Hi. My name is Steve and I want to tell you about the first time my wife, Claire, and I had sex with another couple. We were vacationing with our friends, Debbie and Jason. The house we rented on the beach at North Carolina's Outer Banks was perfect and we were four days into the trip when rain induced boredom started to set in. I was playing "cabana boy": keeping everyone in drinks and food. While we were not drunk, we were certainly relaxed, and I was really only joking when I held up the...
Will you call the next candidate in please?Ah, hello – Its Miss Stephens isn’t it? I’m Alan Peters, this is John Cornwall and this is Jim Squires. I’m pleased to tell you that you have passed through the first interview round so we are able to confirm that you are qualified to do the job, and that there are no further requirements for you to fulfill as far as actually being able to perform in the role. This stage of the interview is purely to get our shortlist of, let me see, five candidates...
Debbie and I sat in the small dressing room and chatted for a few minutes. She explained that Ms. Connor was a partner in the bar and that the back room we were in was a secret – and very illegal. I found out that all the cheerleaders had danced in there at one time or another. She told me in no uncertain terms what would happen to me and my Mom if I ever ratted them out. Of course, my performance was recorded and would be kept as insurance. No men were ever allowed. The customers in the...