Courtesan Ch. 01

I nervously climbed on top of Kelly, pushed my tiny erection into her sopping pussy and started pumping 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. I rolled off of her and buried my face in my hands. I was humiliated.

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 they send me home. Sure it feels good." She laughed. "No, actually it feels wonderful. But Timmy, tonight you made love to me. I had three magnificent orgasms with you. Timmy you're the first guy that has ever been able to do that for me."

I looked at her. "Really?"

Kelly nodded. "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.

I resisted. "Why? Those other guys are much better at fucking you than I am. Why bother with me?"

She shook her head in exasperation. "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; but that still doesn't mean that I don't want you to fuck me."

I thought about this 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 her bed until it was time to go to the dining hall for dinner.

I thought about 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 grinned and 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 and watched her get dressed. After she was done putting on her makeup she turned to me and said, "Timmy are you going to be jealous tonight?"

I thought about her question for a moment and then I said, "I'll probably be envious, but I don't think I have to be jealous."

Kelly stared at me. "I don't understand."

I shook my head. "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. "Yes, now I understand. Envy means that you wish that you had something that someone else has. Tonight you're going to wish that 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 you never have to be jealous. You're the only man I'll ever love."

Kelly Glanced at the clock and her relaxed manner suddenly changed. "Look at the time! It's seven o'clock. Wendell is probably already downstairs waiting for me."

After checking herself one last time in her mirror, Kelly quickly grabbed her purse. As she was opening the door to leave she paused for a moment and then she turned back to me. "Timmy will you please stay here. I would love to be able to see you when I come home tonight. I don't think I'll probably be too late. I expect that after dinner we'll go right back to Wendell's apartment so that he can fuck me. I'm pretty sure that he'll want to take me home as soon as we're finished. The only real 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 there isn't a guy alive 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.

After she was gone I tried to study, but I couldn't concentrate on biology or European History so tried reading a novel instead. 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 pictured them flirting with each other during their dinner. Kelly hung on every word her date said and laughed at all of his jokes.

After dinner I imagined 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.

I was just about to lie down on Kelly's bed so that I could take a short nap when she opened the door and walked into the room.

As soon as she saw me, she smiled. "Timmy I'm so happy to see you're still here. I was worried that 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. "I'm just that kind of a guy, 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 and looked at me. "I'm sorry Timmy, that wasn't very sensitive. Does it bother you when you hear me say that?"

I shook my head. "Not if it's true." Then smiling at her, I asked; "So tell me, why was he so good?"

"Do you really want to hear that?"

"Yes, I think I do. This is a big part of your life right now and I want you to be able to share it with me."

"Are you sure?"

"Yes, I think I am."

"Okay. Timmy, Wendell got three erections tonight. Most guys can only get it up twice and on his third erection I thought he was going to go all night long. I'm not exaggerating Timmy. The last time I think he fucked me for over a half hour." Kelly giggled. "I'm a little sore down there right now."

"Would you rather wait to fool around until tomorrow night?"

Grinning at me, Kelly shook her and said; "Oh no, I think your sweet little tongue is exactly what I need to soothe my poor little pussy right now."

Kelly sat down on the bed next to me and rested her hand on the inside of my thigh. "So what did you do while Wendell was busy fucking my brains out?"

We both chuckled at her crude comment and then I smiled proudly and said, "I wrote a story."

Kelly's eyes lit up. "Really? What's it about? Where is it? Can I read it?"

"It's called, Kelly and Wendell. It's on your computer and yes you can read it."

"Kelly and Wendell? Really? I can't wait to read it. Maybe I could read it aloud while you lick my pussy."

Kelly pulled up her skirt and sat down at her desk. She wasn't wearing any panties. I was certain that I saw her put on a pair when she was dressing for her date so I asked, "What happened to your panties?"

"I let Wendell keep them as a souvenir." Kelly shrugged. "I thought it was the least I could do. The dinner at the Kensington Grill was really expensive."

I laughed. "You shouldn't feel too guilty, after all you did let him fuck you three times."

"Let him? Honey child when I saw Wendell's great big dick I would have begged him to fuck me." Giggling, Kelly spread her legs, snapped her fingers and pointed at the floor near her feet. "Now get over here and start eating my cunt little boy. I've got a story to read."

My entire body tingled with excitement as I got off the bed, crawled between Kelly's parted thighs and pressed my lips against her recently fucked sex.

That started a tradition for us. Whenever Kelly was out on a date I used the time while she was gone to write a story. When she returned home she always read it out loud to me while I kneeled on the floor between her legs and licked her pussy.

As I stood huddled in the doorway of Smithson's Jewelry Store an overwhelming sense of sadness permeated my soul. I tried to tell myself that my low spirits were caused by the cold wet rain and the dark deserted street in front of me, but I knew that wasn't true. I understood exactly why I was feeling so blue. It was the horrible task that I was facing. I wasn't waiting outside my wife's office so that I could meet her, I was hiding in that doorway so that I could follow her.

About a year ago, the demands of Kelly's job increased dramatically. After she was promoted to the position of administrative assistant to the three partners she had to start working longer hours. Her new work schedule included many evenings and some weekends.

At first, these longer hours weren't a problem. I was pleased that Kelly enjoyed her work and of course as her salary increased we both reaped the material benefits of her efforts. Kelly was also very careful to make sure that when she was at home we always had an opportunity to spend some quality time together.

During this time our sex life continued to flourish. Now, don't get me wrong. I'm not trying to present myself as some sort of Don Juan. Believe me, I'm not. I already told you about our first sexual encounter. I have a tiny penis and I tend to cum quickly when I try to have normal intercourse.

Because of that Kelly and I had developed a rather unorthodox sexual relationship. In the bedroom my wife had gradually become increasingly assertive with me. Actually, dominant might be a better term. I hadn't resisted this change, in fact to be totally honest, I'd encouraged it. I'd discovered that I had quite a submissive streak.

Kelly continued to teach me how to please her orally and it wasn't long before she was spending hours on her back enjoying orgasm after orgasm while I licked and kissed her pussy and eventually her ass.

While it was true that Kelly had quickly become the dominant partner in our relationship, she still loved me and once she was well satisfied she always finished off one of our lovemaking sessions by giving me the sweetest little blow job I could possibly imagine.

By the time we were married we were only having intercourse on special occasions. It really wasn't a conscious decision on either of our parts. The truth was, my tiny penis made intercourse frustrating for both of us and we had a much better time when we pleased each other orally. I do have to admit that I spent a lot more time pleasing Kelly than she did me, but I didn't care. I loved eating her pussy and her ass.

Kelly's ass, yes I do lick my wife's asshole, or at least I did when we were still making love. I'll never forget the first time I did it. It was about a month after we started having sex. Kelly didn't have a date so we were spending the evening studying together in her dorm room. Once we were finished we decided to find a hot story on one of the cuckold web sites so that Kelly could read it out loud while I licked her pussy.

I'd discovered these sites one night while I was waiting for Kelly to come home from a date. I was still writing stories about Kelly and her lovers while she was out, but she was very popular and it wasn't unusual for her to have as many as four dates in a week. I was writing a lot of stories and they were starting to get repetitive. I needed some fresh ideas so I began searching the web. I found a veritable treasure trove.

I showed the sites to Kelly as soon as she came home. They got her so excited that we stayed up until dawn reading stories. We quickly fell into a wonderful routine. Kelly would read a story out loud while I kneeled between her legs and licked her pussy. She sometimes had as many as four orgasms during one of our story sessions.

On this particular night we found a story in which a dominant wife made her husband kiss and lick her asshole before she left for a date. Kelly was sitting on the edge of her bed. Her laptop computer was propped up on her night stand. I was kneeling on the floor between her legs.We were both naked. My face was buried in her sopping cunt.

As soon as she read the passage where the husband first kissed and then licked his wife's asshole Kelly grabbed me by the hair and lifted my face out of her pussy. "Timmy did you hear that?"

I nodded. "Yes I did."

Shaking her head, Kelly said; "That is so hot. I don't know how she could get her husband to do that for her. He must really love her."

I'd been licking Kelly's pussy for about fifteen minutes. I was very excited and feeling extremely submissive. Looking up at Kelly, my face glistening with the moisture of her arousal, I said; "I love you that much."

Kelly stared at me. After a moment she said, "Timmy are you saying that you'd be willing to do that for me?"

I smiled at her. "Yes I am."

Kelly gasped, but she was also grinning. "When?"

"How about right now."

"Timmy are you serious?"

"Yes, I'm very serious."

Kelly was silent for a moment and then in a mildly apologetic tone of voice, she said; "Timmy, I don't think I can do that for you. It's not that I don't love you, but..."

I patted her knee. "It's okay, I don't think you should do it for me. I wouldn't seem right."

I watched Kelly while she thought about what I'd just told her. Finally she looked at me and said. "I think I understand. It's kind of the same thing as when you told me that you still wanted to be faithful to me even though you knew that I was going to continue dating other guys."

I nodded. "Yes, I think that's right."

Kelly considered that for a few seconds and then she said, "It doesn't seem like it's fair, but I think that might be what makes it so much fun."

I grinned at her and said, "I think so too."

Giggling, Kelly lay down on her stomach with the side of her face resting comfortably on a pillow. My entire body was tingling with excitement as I got up on the bed and positioned myself between her thighs.

When she felt me spreading the soft cheeks of her gorgeous ass Kelly breathlessly said, "Timmy this might be the most exciting thing I've ever done."

I slowly lowered my face to Kelly's rear. When she felt my lips touch her tiny anus she shivered with excitement. At first I just kissed her. Neither of us said anything. We didn't have to. We both understood exactly what was happening. I was pledging myself to my goddess.

Finally I tentatively extended my tongue and tasted Kelly's asshole for the very first time. It excited me and I wanted more so I pushed my tongue into her.

As soon as she felt me exploring her Kelly got up on her hands and knees to give me freer access to her rear. I pushed my tongue even deeper into her. She responded by grinding her ass against my face. I reached between Kelly's legs and started rubbing her engorged clitoris while I continued kissing and licking her asshole.

That put Kelly over the edge. She gasped, I felt all of the muscles in her body flex and then she screamed. It was a volcanic orgasm.

Afterward we searched for more stories that featured ass licking. It wasn't long before we encountered the term, anal worship. Kelly thought it was an apt description. From that night on, whenever we made love Kelly would roll over onto her stomach and say, "I think it's time for my little boyfriend to express his love with a little anal worship."

I'm not sure which of us enjoyed it more, but I did know that the role that each of us was destined to play in our relationship was gradually becoming more clearly defined.

After Kelly received her first promotion I took on the exclusive responsibility for doing all of the household chores. The shopping, cooking, cleaning and laundry all became my duties. I didn't object. In fact I liked it. It also made sense to both of us. My job was much less demanding than Kelly's and while neither of us had ever voiced this, I'm quite certain that we both saw it as appropriate. My wife's dominance was slowly moving out of the bedroom and into the rest of the house. Bit by bit she was assuming the role of the dominant bread winner and I was becoming the submissive homemaker.

Kelly enthusiastically embraced her developing role. She loved being the dominant partner in our marriage and she played her part to the hilt. When I served her a dinner that she especially enjoyed or she came home and found the house particularly clean she would joke that I had become the perfect housewife. My wife would giggle and tell me that I was the ideal mate for her. I could clean, cook and give wonderful head. The most amazing part is that I found her praise both gratifying and exciting. I loved my submissive status every bit as much as Kelly loved her dominant position.

Our life was still something out of a storybook. It maybe wasn't the typical storybook of our culture, but it was one that worked very well for us. Kelly worked hard at her job and supplied us with an ample flow of money. I kept the house and diligently tried to support her by trying to meet her every need.

It was last winter when I first noticed that things were beginning to change. Now, as I look back, I realize that the changes had been gradually occurring for almost a year, but they accelerated when Kelly was promoted to the position of special assistant to Martin Jackson. While that was just before Christmas I didn't really begin notice that something was happening until the first Friday in February.

Kelly got home from work at about six. I was happy, on the three previous Friday's she'd had to work until ten or eleven o'clock. As soon as she walked into the house she kicked off her shoes and called to me, "Timmy honey, bring me a martini."

I was already making it. I knew my wife and I prided myself on my ability to anticipate her needs. Once her cocktail was ready I put it on a tray. Kelly always seemed to be pleased when I brought things to her on a tray. I set the daily newspaper next to her drink and carried the tray into the living room.

My wife was sitting in her favorite chair. I set her cocktail and the newspaper on the table next to her and bowed politely. Kelly smiled at me and said, "Thank you Timmy, what's for dinner?"