Jason Mathews, Attorney at law
It was 7:30 on a blustery night in late October. The sun had gone down over an hour earlier. A light drizzle and the bitter bite of the frigid north wind made it a miserable time to be outside. Sadly I had no choice. I was waiting for my wife.
I stood huddled in the doorway of Smithson's Jewelry Store making a futile attempt to stay warm by pulling the collar of my coat up over my ears and blowing on my hands. It was a Thursday night. The store had closed at six. The sidewalk in front of me was deserted and dark. The only illumination came from the street light on the corner and the lights surrounding the main entrance to The Whetmore Building directly across the street.
The firm of Jackson, Tyler and Reynolds occupied the entire fifty-second floor of the fifty-four story Whetmore Building. My wife, Kelly Mason worked for Jackson, Tyler and Reynolds.
JTandR as it was commonly known to it's employees was an elite investment firm. Kelly was an administrative assistant to Martin Jackson, the senior partner and Chief Executive Officer of JTandR. Martin Jackson was an extremely wealthy man. He was also one of the city's most influential power brokers.
My name is Timothy Jamieson. Everyone who knows me calls me Timmy.
I guess you could say I was a writer of sorts. I worked for one of those local advertising newspapers. You know what I'm talking about, they're those skinny little publications that get stuffed into your front door a couple of times each month. The one I worked for was called The Southwest Crier. I edited advertising copy. The job didn't pay very much, but the hours were good. I also got a lot of extra time to work on my novel.
Oh yes, I was one of those guys who had a dream. I still have it. Someday I'm going to write a best seller, or at the very least a book that gets published.
My wife earns a lot more money than I do. Actually the disparity in our incomes makes mine nearly inconsequential. The Crier pays me just over two thousand dollars a month. During her first year at JTandR Kelly earned nearly a hundred and fifty thousand dollars. This was her second year. She was now on track to make almost double that.
Kelly's rise in the firm has been meteoric. JTandR hired her right out of college. She started as an assistant to one of the corporate analysts. Apparently she made an immediate impression, because four months later she was working as an assistant to the three partners and the following December she was made a special assistant to Martin Jackson. As I already mentioned, he's the head honcho.
My wife is a gorgeous 5'4" fireball with naturally blond hair.
There's an athletic club located on the third floor of the Whetmore Building. JTandR provides a membership for Kelly as part of her compensation. She makes daily use of the exercise machines. Those regular workouts help my wife maintain a trim athletic figure that draws admiring glances from every healthy adult male she encounters.
Of course those glances may also have something to do with Kelly's most notable attribute. Maybe it would be more accurate to say attributes. My wife is well endowed. I mean spectacularly well endowed. We're talking about a pair of double D's on a five foot four inch, one hundred and fifteen pound frame.
Kelly laughingly refers to her breasts as both her gift and her curse. While she freely admits that since the age of fifteen her bosom has garnered her privileges, male attention and special treatment that other girls didn't get, she's also quick to point out that her huge breasts and blond hair have made it very difficult to get people to accept her as anything other than a mindless bimbo.
I suppose that was one of the reasons that Kelly was attracted to me. Ironically, I'm not a breast man. I happen to be an avowed butt man. Now my wife does have a very cute little bottom, but it's no where near as spectacular as her bust.
Actually I was originally attracted to Kelly's brain. We met as Sophomores at Kelroy College. We were enrolled in the same creative writing class. My wife loves to write poetry and she's very good at it. About three weeks into the semester she was asked to read one of her poems to the class. The poem she chose described a little girl's feelings as she chased a butterfly through a rose garden on a sunny summer afternoon. It took my breath away.
After class I waited in the hallway for Kelly. I really don't know where I found the courage to do it. I was a pathetically shy, slightly effeminate, scrawny little wimp. Kelly was gorgeous and very popular. Kelroy was a small private college. Everyone knew everything about everybody. I was well aware of the fact that Kelly only dated handsome fraternity guys and muscular football players. She was way out of my league.
When she stepped out of the classroom I walked up to her and just barely managed to stammer out the words, "Kelly I thought your poem was one of the most beautiful pieces of writing I've ever heard."
I'll never forget her response. My future wife stared at me for a moment and then she started to smile. "Really? Do you mean that?"
Encouraged by Kelly's smile, my confidence grew. I smiled back and said, "Yes I do mean that. When you were reading it I actually felt like I was in the garden with the little girl."
"I have lots of poems. I write them all the time. Would you like to hear some more?"
I nodded. "Yes, I'd like that very much."
"Are you doing anything right now?"
I shook my head. "No, but..." I was starting to get scared.
Kelly noticed my distress. In the softest most gentle voice I've ever heard she said, "There's nothing to be afraid of. I promise I won't hurt you." She took my hand. "Come on, let's go to my dorm room. I'll make us some hot chocolate. I'll read some of my poems to you and then maybe you could read something you've written."
We became immediate friends and it wasn't long before we were best friends. We wrote poetry together, studied together, read novels together, watched movies together and listened to music together. Two weeks after that first meeting we were nearly inseparable.
The only thing we didn't do was date. Kelly continued her habit of exclusively going out with handsome fraternity guys and muscular football players. To make matters worse she had a reputation for being easy. The campus rumor mongers all called her the blow job queen of Kelroy College. On Friday and Saturday nights I not only had to sit at home alone, I had to do it knowing that there was a high probability that the girl I was madly in love with was getting fucked by another guy.
I never complained, but one afternoon I did gather enough courage to ask Kelly about it. I'll never forget that day. We were studying in her dorm room. I'd already fallen desperately in love with her and I had to know if the rumors were true.
I set my book down and nervously watched Kelly. She was engrossed in her own book and didn't notice me. I made a little noise. She looked up. When she saw me staring at her she asked, "What is it?"
"Can I ask you a question?"
"Sure Timmy, you're my best friend. You can ask me anything."
"It's very personal."
Sighing, Kelly set her book down. "I suppose you want to know about the rumors?"
"Yes, but you don't have to tell me if you don't want to."
Kelly shook her head. "No, I meant it when I said that you could ask me anything." She took a deep breath and then she quietly whispered. "I'm sorry Timmy, but they're all true. I love sex and I especially love sucking cocks. I probably am the blow job queen of Kelroy College."
I stared at the floor. Kelly's frank admission had stunned me. I didn't know how to respond.
Reaching over, Kelly took my hand and said, "Timmy, I'm sorry if I shocked you, but you're my best friend. I think I'm falling in love with you. I don't want to lie to you. I don't ever want to lie to you. Do you hate me now?"
Looking at Kelly, I shook my head and answered, "I'm falling in love with you too. I could never hate you."
She kissed my cheek and then she pushed me down on the bed. Once I was lying on my back she unbuckled my belt, unzipped my jeans and pulled out my tiny cock.
I'd seen enough other guys in locker rooms after gym classes to know that I had a small penis. I looked at her with an embarrassed expression and said, "I'm sorry, it's not very big."
Kelly smiled at me. "I get to play with plenty of big cocks. This one is yours and because it's yours it will always be my favorite."
She leaned over, kissed the tiny head of my erect penis and then she put it in her mouth and started sucking it. Kelly had caught me completely off guard. Even in my wildest dreams I'd never imagined that something as wonderful as this might happen.
I came immediately. I tried to warn Kelly, but there really wasn't much time. As it turned out, it didn't actually matter. Even after she realized I was ejaculating Kelly kept my cock in her mouth and greedily sucked up all of my semen.
As soon as I was finished ejaculating Kelly looked up at me and smiled. "It's okay Timmy, you can always cum in my mouth. I love the taste of a guys semen."
She sat up and pulled her sweatshirt over her head exposing her huge breasts. Tossing the shirt onto her dresser, she asked, "Timmy, do you like my big boobs? Lots of guys on this campus would give anything to be able to touch them and now you get to play with them anytime you want. All you have to do is ask."
I didn't say a word. I couldn't speak.
Kelly laughed. "You're absolutely speechless aren't you baby?"
I nodded.
Kelly unfastened her jeans, pulled them down to her ankles and kicked them off. All she was wearing was a tiny pale blue thong.
I took a deep breath and whispered, "You're beautiful."
"There isn't another boy in the entire world that I would rather have looking at me." Kelly lay back on her bed, hooked her thumbs into the waist band of her panties, pulled them down to her ankles, pushed them off with her feet and lasciviously spread her legs. She was shaved.
I stared at her cunt. I couldn't help myself. I'd looked at lots of pictures of naked women in magazines and on the Internet, but this was the first time I'd ever seen a naked pussy in real life.
Noticing my fascination, Kelly laughed, "This is the first time you've ever seen a girls cunt, isn't it Timmy?"
My mouth dropped open in shock. Kelly was my goddess. I'd never imagined that she could use such a coarse word.
Chuckling at my dumbfounded expression, Kelly said, "You'd better get used to that Timmy, I love to talk dirty when I'm making it with a guy."
I was completely befuddled. I didn't move. Actually I was paralyzed. I couldn't move. I just sat on the foot of the bed and continued staring at Kelly's naked sex.
She started laughing. "You could spend the rest of the evening looking at my pussy, but I was sort of hoping you might want to try licking it."
I gasped when I heard her suggestion.
Kelly misunderstood the gasp and frowned. "Don't you want to lick my cunt? Don't worry, it's not dirty or nasty, it's fun." She smiled at me. "I did something for you, now I think it's only fair if you to do something for me."
I had to pull myself together. Kelly was getting the wrong idea. I not only wanted to lick her pussy, doing it was my ultimate fantasy.
Quickly shaking my head, I said, "No, I want to do it. I want to do it more than anything in the entire world."
She giggled. "That's a lot. Well what are you waiting for big boy? Go for it."
I positioned myself between Kelly's parted thighs, took a deep breath and tentatively kissed the lips of her already moist sex.
"Oh yes Timmy, that's right. Just kiss me for a minute. That feels so good."
Kelly's response gave me confidence. I kissed her again, only this time I was more aggressive. Kelly quivered. I closed my eyes and kissed her even harder. Now it was her turn to gasp. I felt her moisture on my lips. I knew that girls got wet when they were excited, but this was the first time I'd ever felt that moisture.
"Timmy use your tongue, give my pussy a French kiss."
I pushed my tongue into Kelly and for the first time in my life tasted a woman's sex. My entire body tingled with excitement.
"Lick me Timmy. Lick my pussy like it's a big lollipop." She giggled. "That's what I always do when I start sucking a cock."
A willing, eager student, I did exactly what I was told to do. As soon as I started licking her, Kelly responded by tittering with delight. I quickly realized that I got a thrill from giving pleasure to this beautiful woman. I began to experiment. Kelly held her breath when I licked her with long slow strokes and she started giggling again when I licked her quickly.
I decided to try teasing Kelly. I placed my tongue at the base of her pussy and began a tortuously slow climb through her cleft to the peak of her cunt.
When she realized what I was doing Kelly started giggling and said, "Timmy that's cruel."
I looked up at her. "Do you want me to stop?"
She burst out laughing. "Absolutely not!"
I pushed my tongue back into her sopping pussy and continued my climb. When I reached the top I found her engorged clitoris. I'd read enough erotic stories on the Internet to know exactly what it was. I kissed it.
Kelly shrieked. I got scared and pulled back.
She sat up. "No baby, don't stop. That was wonderful. Please kiss me there again."
As I said earlier, I'm an excellent student. I dutifully follow directions. I kissed Kelly again only this time I used my tongue when I kissed her. She shrieked again, but this time I didn't stop. This time, while I kissed her I also flicked her clit with the tip of my tongue. Kelly started laughing hysterically. I kept flicking her clit with my tongue. She went wild and responded by grinding her hips against my face.
Suddenly, without any explanation or warning, Kelly stopped laughing and grinding her hips. I felt all the muscles in her body tighten. She took a deep breath. For a moment she lay perfectly still and then, after taking another deep breath she shrieked.
Disconcerted, I pulled back.
Kelly's entire body shook and she started laughing again. Quickly realizing that she was having an orgasm I relaxed and watched her. Several seconds passed. Gradually her body stopped shaking and her laughter turned into low cries. The cries became soft whimpers. Several more seconds passed and then she was quiet.
Kelly lay perfectly still for almost a minute. Finally she sat up and smiled at me. "Timmy you just gave me an orgasm. Very few guys are capable of doing that. Sweetheart, you just became my favorite lover."
I knew that her words were meant as a compliment, a wonderful compliment, but there was also subtle message in those words. It was a message that made me feel sad. When Kelly told me that I'd just become her favorite lover she'd also implied that I wouldn't be her only lover.
I couldn't help myself. I bit my lower lip and stared sadly at the floor.
Kelly studied me. After a moment she asked, "Timmy, what's wrong? We just had wonderful sex."
I looked at her and quietly said, "If I'm your favorite lover, it also means that I won't be your only lover."
Kelly thought about that for a second and then she sighed. "Timmy you're my best friend and I think I might be falling in love with you. Baby I promise you that you're the only guy who has my heart, but Timmy honey, I'm afraid you're going to have to share my body. At least for now." She smiled at me. "Sweetheart, I love sex. At this point in my life it's a huge adventure for me." Holding up her large breasts, she giggled and said, "You have to admit that I'm built for fucking." She picked up my hand and held it to her breast. "Baby, before I finally settle down I want to experience as many different men as I possibly can." Kelly leaned over and kissed my cheek. "But I do promise you that you'll always be my number one man. Can you live with that?"
I considered what Kelly had just told me. After a moment I smiled and said, "Yes, I think I can."
Kelly sighed with relief. "Timmy, thank you for being so understanding." She kissed me lightly on the lips. It was a tender kiss, not hot and passionate, but filled with love. She reached down and wrapped her fingers round my penis. It was sticking straight up.
Giggling, Kelly said, "It looks like somebody is ready for round two. How would you like to eat me again and after I cum maybe you'd like to try fucking me."
I stared at her. I couldn't believe what I'd just heard.
She grinned at me. "If you're going to be my number one lover you're going to have to fuck me once in a while."
"Is it safe? I don't have any condoms. I don't want to get you pregnant."
Kelly shook her head. "Timmy you might just be the nicest boy in the entire world. Yes, it is safe. I'm on the pill, but thank you for asking. Most guys aren't so considerate. It should also be safe for diseases. You're a virgin so I'm not worried about you and I always make the guys I date wear condoms." She poked me in the stomach. "You're the only guy who gets to fuck me bareback." She giggled again. "But you'd better not let me catch you fooling around with any other girls."
"You don't have to worry about that. I won't ever play around with other girls. I promise."
Kelly stared at me."Timmy that's silly. I was just teasing you. You don't have to make that promise to me. Especially after I just got done telling you I'm going to keep dating other guys."
I shrugged. "It's not exactly like there's a crowd of girls lining up to go out with me."
Kelly laughed. "When the other girls on my floor find out that the scream they heard a little while ago was me having an orgasm because you were eating my pussy, you might just find yourself overwhelmed with invitations."
Suddenly a little thrill rippled through me. At the time I didn't know why the idea excited me so much, I just knew that it did. Later I figured out that it was the first of my submissive cuckold fantasies coming to the surface. I kissed Kelly on the cheek and said, "I give you permission to freely date as many guys as you want, but I promise that I'll always remain completely faithful to you."
Kelly stared at me. "Timmy are you being serious? Do you really want to make that promise?"
I nodded.
She took a deep breath. "Baby that is so hot." Kelly smiled at me and then she lay back on the bed and spread her legs. "Eat me Timmy. Give me pleasure, make me cum."
I buried my face between Kelly's thighs. At that moment I longed to give this wonderful woman all the pleasure she desired.
I brought Kelly to two more orgasms with my tongue. After she recovered from her second orgasm she lay back on the bed, spread her legs and wiggled her finger at me. "Come on studman, it's time."
Wildly excited, I climbed on top of Kelly, pushed my tiny erection into her sopping pussy and started pumping away like a madman.
Kelly giggled. "Timmy honey, you have to put it in me before you start doing that."
I stopped moving and looked at her. "I am inside you." Suddenly I realized the implications of her comment. Humiliated, I rolled off of her and buried my face in my hands.
Kelly sat up, put her arm around my shoulder and whispered to me. "Timmy I'm sorry, I didn't..." She stopped. I think she realized that there was nothing she could say that would make the situation better. Instead she just held me. After several minutes she whispered into my ear, "Timmy you're still my favorite lover and your cock is still my favorite cock."
I laughed. It was a sarcastic laugh. "Oh yeah? You can't even feel it when I'm making love to you."
"No Timmy, you're wrong. When you're making love to me I do feel it." She sighed. "Yes, it is true. You have a tiny penis and maybe it doesn't feel as good as it does when a guy with a big cock is fucking me." She stared into my eyes. "Timmy those guys are just fucking me. They pump their big cocks in and out of my cunt until they shoot their load and then I go home. Sure it feels good. No, actually it feels wonderful." Kelly smiled, "But Timmy, tonight you made love to me. I had three magnificent orgasms with you. You're the first guy who's ever been able to do that for me."
"Really?"
"Yes, really."
I smiled. I was starting to feel better again.
Kelly sensed the change in my mood. "All right cowboy, it's time to get back in the saddle and start riding again." She grabbed my arm and tried to pull me back on top of her.
While I was starting to feel better, I was still bothered by self doubt and insecurity. I resisted her. "Why? Those other guys are much better at fucking you than I am. Why bother with me?"
Shaking her head in exasperation, Kelly said, "Because it's you dummy. I love you and I want you to fuck me. Yes, there are other things that you do better and there are other guys who are better at fucking me than you are. That still doesn't mean I don't want you to fuck me."
I thought about that for a moment and then I said, "Okay, but you have to promise that you won't laugh while I'm doing it."
Kelly rolled her eyes. "Okay, I promise."
It was wonderful and afterward we cuddled in Kelly's bed until it was time to go to the dining hall for dinner.
I smiled as I stood freezing in the doorway of Smithson's Jewelry store. That evening was one of my fondest memories.
My thoughts drifted to the first time Kelly went out on a date after we'd become boyfriend girlfriend. It was the Friday night after that wonderful Tuesday when we first made love. A fraternity guy named Wendell Foster was taking her to dinner at the Kensington Grill. The Kensington Grill just happened to be the fanciest restaurant in our city.
When Kelly told me about the date she said, "Wendell's just taking me to that fancy restaurant to impress me. He thinks it'll give him a better chance to get into my panties." She winked at me. "A hunk like Wendell could buy me a hot dog at a convenience store and still get into my panties."
We both laughed at her joke.
The night of her date I sat on the bed in Kelly's dorm room watching her get dressed. After she finished putting on her makeup she turned to me and asked, "Timmy are you going to be jealous tonight?"
I thought about her question for a moment and then I answered, "I'll probably be envious, but I don't think I have to be jealous."
Kelly stared at me. After a moment she said, "I don't understand."
"Kelly Mason, you're an English major. You know the difference between jealousy and envy, don't you."
"Of course I do." She took a second to think and then she smiled. "I get it. Envy means that you wish you had something someone else has. Tonight you're going to wish I was with you rather than Wendell."
I nodded.
She continued. "But jealousy is the fear that someone you love is falling in love with someone else." Kelly stood up, walked over to the bed and kissed me. "Timmy Jamieson, you never have to be jealous. You're the only man I'll ever love."
As she kissed me again, Kelly glanced at the clock. Her relaxed manner suddenly changed. "Look at the time! It's seven o'clock. Wendell is probably already downstairs waiting for me."
Kelly kissed me once more, checked herself in the mirror and grabbed her purse. As she was opening the door to leave she paused. Turning back to me, she said, "Timmy will you please stay here. I would love to be able to see you when I get home tonight. I don't think I'll probably be too late. As soon as we finish dinner we'll go to Wendell's apartment. After we're done fucking I'll make him take me home. The only question is how often can he get it up." She giggled. "If he turns out to be a real animal I'll give him a blow job to slow him down a little. They don't take much time and I've never met a guy who doesn't love them."
I smiled at Kelly. "I would love to wait here for you."
She leered at me. "Will you eat my pussy when I get back? I promise I'll make Wendell wear a condom."
I laughed. "I'm already looking forward to it."
Kelly smiled and then she sighed and said, "Timmy I really do have to go. I should be back around midnight."
As I nodded to her she blew me a quick kiss and ran out the door.
Once Kelly was gone I tried to study, but I couldn't concentrate on biology or European History so tried reading a novel. That didn't work either. I couldn't stop thinking about Kelly and Wendell. In my mind I could picture every second of their date.
I saw them walking into the restaurant holding hands. I imagined them flirting with each other during dinner. Kelly hung on every word Wendell said and laughed at all of his jokes.
After dinner I pictured Kelly taking Wendell's arm. Pressing her body against his, they walked out to his car. When they got to his car...
I shook my head. Enough! I was going crazy. I closed my eyes and rubbed my forehead. I didn't know what I was going to do. Sitting in Kelly's room waiting for her to come home was turning out to be unbearable. Suddenly a solution popped into my brain. It was obvious. I sat down at Kelly's desk, turned on her lap top computer and started typing.
The title of the story was "Kelly and Wendell". It was almost midnight by the time I finished it. I hoped that Kelly might want to read it when she got back from her date, so I left her computer turned on.
Tired, I decided to lie down on Kelly's bed and take a short nap. As I was closing my eyes she opened the door and walked into the room.
As soon as she saw me, Kelly smiled. "Timmy I'm so happy you're still here. I was worried you might have gotten bored and decided to go home."
I shook my head. "No, I told you I'd wait here until you got back." I shrugged. "That's just the way I am. I'll always wait for you."
Kelly grinned at me. "And that's why I'm falling madly in love with you Timothy Jamieson."
"So how was your date?"
Sighing, Kelly said, "It was wonderful. Wendell is an absolutely magnificent fuck..." Suddenly she stopped. Looking at me with apologetic eyes she said, "I'm sorry Timmy, that wasn't very sensitive.