Dayla and Will

Dayla Prichert sat up in bed and wondered what just happened. She looked down at the man lying next to her and smiled. They'd been dating for two months now and over the course of those two months she learned that Will Conti was more intelligent and talented than any man she ever dated; tonight she found out he also had a beautiful cock and knew how to use it. Dayla wondered how many times she had cum, she lost count after the first hour.

Dayla met Will just over two months ago at her regular hang out. She and a few of the ladies from work were blowing off steam on a Friday night in Murphy's Tavern. Dayla needed a couple drinks; it had been a busy week at work and the guy she'd been seeing for the past year didn't show up today or answer his phone. It didn't help that George was a co-worker (in act, he was her immediate supervisor) and it certainly didn't help that she suspected George wasn't the kind of man to be faithful.

From across the bar Will noticed the gorgeous blonde wasn't with the stiff he'd seen her with on previous evenings. He didn't think they were exclusive because she didn't have a ring on her finger and he had seen the same guy at a club last week with a different woman. Will wasn't the kind of guy to make a play for another man's woman; but given the circumstances, this looked like the perfect opportunity to introduce himself. Will asked the barmaid to send a round of drinks to the four ladies at the blonde's table; when the drinks arrived, Will walked over to say hello.

Much to Will's surprise, the blonde was as beautiful up close as she was from across the room. Even better, she had a friendly, charming manner. It was apparent to everyone at the table why Will was there, but he had bought them all a drink and was bright enough to spend as much time talking with each lady as he did with the object of his pursuit, so the ladies gave him a pass and let him stick around.

Will didn't overstay his welcome, but did get Dayla's phone number before leaving (he hoped it was really her number, some women are apt to give out a phony number to get rid of an unwanted Romeo). As soon as Will left the tavern, all three ladies were giving Dayla advise; it was unanimous, Dayla would be a fool not to accept a date, if and when Will called. Phoebe was the most adamant and, as usual, the funniest.

"Girl, if you don't say 'yes' when he calls, you just let me know. I never dated a white boy before, but for that one I'd make an exception."

The other ladies laughed because they knew Phoebe better than that, Phoebe was known for her undying love and affection for her husband, Jeffery.

Will did call later that week and Dayla accepted his invitation for their first date the next Saturday afternoon. Will took Dayla to the Art Institute. Dayla hadn't been there in at least five years and never with a man who had an intimate knowledge of both classical and modern art. It wasn't as if Will was trying to impress Dayla with his knowledge, it was more like a conversation, drawing out her likes and dislikes. By the time Will dropped Dayla off at her apartment later that day, they had plans to spend their next date at Wrigley Field.

During the game, Will confessed his ignorance regarding baseball and it was Dayla's turn to enlighten him on the nuances of the game. It was Will's most enjoyable baseball game since his father took him to Wrigley Field when he was 10 years old, just before his dad's untimely death from an industrial accident.

As the weeks flew by Dayla spent more of her free time with Will and a lot less time with George. After the fourth week, Dayla spent the last night in George's bed. No announcement was made, Dayla just quit going out with George and George was too busy with the other women he was seeing to notice; at least for a while.

Will knew that Dayla was still seeing someone during those first few weeks, the relationship was in its infancy and there was no expectation of exclusivity. But after the fourth week, Will noticed Dayla was available any time he asked her out.

Neither Will nor Dayla shared much about their respective past lovers during those first few weeks; each having reasons for avoiding the subject. It was a sign of the times that both were dating, and sleeping with, co-workers. Will only recently broke it off with Amanda Potter, one of the IT techs at the office.

Throughout the first two months of courtship Dayla discovered Will's knowledge of art was just the tip of the iceberg. Will had an extensive CD collection spanning classical, country, rock and jazz. One afternoon they spent listening to the CSO in Grant Park. Will was the only man she knew that could spend the morning reading Dostoevsky and the afternoon fixing all the maintenance problems in her apartment that the Super never found time to fix. He even spent one Sunday with her father getting his vintage Triumph TR4 tuned and running.

The phone call she received from her folks that night made it very clear both her mom and dad considered Will a 'keeper'. She thought the same, but wondered why Will hadn't tried to sleep with her, she silently worried that this could be Will's flaw; was he asexual, did he have a physical deformity or inability to perform, or maybe just embarrassed by the size of his equipment?

Dayla was determined to find out, but didn't have the chance because the following Friday Will asked Dayla to wear something 'nice' and took her to Le Colonial on Rush instead of their usual Friday night at one of the neighborhood taverns. As soon as the waiter left with their drink orders, Will got right to it.

"You're probably thinking I'm gay or something since I haven't tried to take you to bed, right?"

Dayla was tempted to tell a white lie, but something inside her knew this was the wrong way to begin the next phase of their relationship. She answered him honestly.

"Yes, the thought crossed my mind. That and some other reasons; including maybe you don't find me attractive or sexy."

"Nothing could be further from the truth; you are, without a doubt, the most attractive woman I've ever dated."

Dayla smiled at the compliment. "OK, that's settled; thank you. But does that mean we're back to you being gay?" Dayla said this making certain he understood she was trying to keep the conversation light, but secretly she crossed her fingers.

"No, I'm not gay -- as Seinfeld said -- "not that there's anything wrong with that", and I'm hoping we can correct any other misconceptions relating to how attracted I am to you and whether I have performance issues. That thought probably crossed your mind as well, right?"

Dayla answered his question with another smile, she was caught and didn't have to say a word to confirm that this too was one of her fears.

About this time the waiter brought their drinks, they asked if they could have a few more minutes before ordering dinner. As soon as the waiter agreed and left, Will continued.

"Dayla, I waited this long for a few reasons. One, because I knew you were involved with your boss. We haven't talked about it, but I get the feeling that relationship has ended. Two, I have fallen hard for you, it's only been a couple months, but I'm in love with you and I hope you feel the same. Last reason, I want our first time to be making love, not screwing and before we make love for the first time, I want us to be exclusive. No more dating, kissing, screwing, whatever, any other people. I promise not to do anything with any other person that I wouldn't do if you were in the room with me; and I'd like you to agree to respect me in the same way."

"Will, I feel the same way. Yes, I love you.

"Yes, I want to take this relationship to the next level. I think you may be the man I spend my life with and raise a family, but we need more time together before making that kind of lifetime commitment. I'm looking forward to spending the time with you making certain.

"Finally, you're right. George and I ended our relationship over a month ago, but I've been negligent and haven't 'officially' told him. But I will and very soon."

With that settled, Will resisted the temptation to skip dinner and head straight to his apartment. They did skip dessert. Soon after the front door closed both were naked, only stopping their kisses to remove each article of clothing and again when Will stood back to view the vision of Dayla's extraordinarily beautiful body.

Will took her by the hand and led her to the bedroom where they made love for the first time. That's when Dayla discovered Will had nothing to hide, his cock filled her completely. She couldn't help but stare when she saw it hard and tried to grasp it in her hand. Her fingers didn't reach around the base and at least as much was outside of her grip as she had in her hand. There was very little foreplay, the last few weeks were all the anticipation either of them needed. Dayla was wet and as she laid on her back and pulled him toward her vagina, his cock slid in until their pubic bones met. They looked in each other's eyes, kissed and Will slowly made love to his woman.

Dayla hoped after those first few hours that this was the man she would spend her life loving, but now faced a dilemma. Dayla agreed enthusiastically with Will that their relationship would be exclusive. He made it very plain and simple, if they were intimate, no other people could be in their lives; no dates and certainly no other sex partners. Dayla was in love with Will and was thrilled Will felt the same way.

The dilemma? Dayla had been dating her boss at the bank for the past year and as things got more serious with Will, Dayla was avoiding George Tinker. George eventually noticed and was starting to press Dayla for the reason they hadn't had sex for the past month. On Monday Dayla would tell George it was over and that would make the situation at work very uncomfortable. It sounded so simple in the restaurant. Dayla fell asleep in Will's arms after saying a prayer that things would work out.

It didn't, of course. As the words left Dayla's lips Monday morning in George's office, she could see the anger in his eyes. George was a proud man, women didn't dump him, he dumped women. The only thing that prevented George from losing his temper and screaming at this little bitch was he knew that on the other side of the closed office door were five employees who would hear him shout. Talk about losing face!

George did the only thing his egotistical mind could think to do, he told Dayla it didn't matter to him because he's been sleeping with other women the entire year they've been dating and that she was a lousy fuck. Dayla walked out of the office wondering what possessed her to have spent a year with this poor excuse of a man.

Will and Dayla continued to fall more in love and continued to spend most weeknights and weekends pleasing one another. One night after a wonderful round of sex Dayla couldn't stand it any longer, she leaned on her side with one hand holding up her head and the other gently playing with Will's pubic hairs.

"Tell me how you became such an incredible lover."

Will laughed until he saw the look in her eyes. By now he knew Dayla well enough to know this was a serious question and part of her was afraid of the answer. Will stopped himself from making light of her question.

"First tell me - why do you want to know?"

"I'm almost afraid of the answer. You either had many women in your past or some femme fatale; either way I feel like I'm competing against a stacked deck."

Now Will had to work even harder not to laugh.

"Dayla, you have no competition. I'm trying not to laugh because I've had similar questions concerning your past. I can't help but wonder where you learned some of the things you do with your body. Did some exotic past lover teach you the Kama sutra? Please tell me it wasn't George."

"God, no! I don't want to get into that, but please believe me when I tell you that George couldn't please one of those blow up dolls. I think you're changing the subject. How do you know how to make love like you do?"

The full moon was shining through the window and lit up Dayla's beautiful blue eyes, her blonde hair practically glowed. It was a moment of truth in their relationship and Will was determined to pass this test, no secrets.

"I was very fortunate. My senior year at university I became the lover of one of my college professors. We weren't in love, but we liked each other with a passion. She was very vocal when it came to giving me direction on how to please her. The affair lasted my entire last year at school, she ended it the day after graduation. She gave me a round trip ticket to Europe, a Europass train ticket and a Lonely Planet guidebook. She told me to have a good time and forget about 'us'. She knew I was having feelings toward her, feelings she wasn't about to reciprocate.

"I spent five weeks in Europe; the first two weeks being a mope because I missed her while touring Paris, 'the city of love'. The next two weeks with a group of Australians in Southern France and Northern Italy. My last week was spent on Ibiza with an Italian co-ed. I came back to the States with a deep appreciation for the knowledge my professor had imparted."

Dayla continued to tease Will with her fingertips as he talked; by now her fingers had moved south from his pubic hairs to his cock. As she wrapped her fingers around it she was again thrilled when her fingertips didn't meet; she squeezed and moved up and down until it was rock hard. Dayla raised herself and planted the mushroom head into the lips of her labia. As she settled down and felt it fill her she said, "Please thank your professor for me if you get a chance, but remember our deal -- we're exclusive. No reliving old times."

With the full length of Will completely filling her, Dayla stopped.

"When did you lose your virginity?"

Will couldn't believe this woman. Straddled on top of him, squeezing his cock with her vagina, and she wants to talk?

"Total cliché. It was with the girl I dated in high school, after our senior prom. I was a virgin; she said she was, too, but I have my doubts. It didn't matter in the long run because I succeeded in losing my virginity before graduating, that's what counted at the time."

"Losing your virginity was your high school goal?"

"Yes, and it wasn't my first attempt. When I was a junior, Jon Meyer and I were working as busboys at a deli and we both decided we didn't want to graduate virgins, but neither of us had any prospects, so we figured we'd go to a whorehouse and have prostitutes do the deed. Trouble was, we didn't have a clue where there was a house of ill repute. So, we asked the guy who washed the dishes. He gave us an address near Comiskey Park, on the southside.

"Jon and I took the EL down to 47th and no sooner do we get off the train before five or six kids start chasing us down the street, it was quite obvious we didn't belong on their turf.

"Jon and I are scared shitless, but we run into a tavern just ahead of these guys. You should have seen the look on the faces of the people in that tavern when two white kids come charging in yelling, "help us". I'll never forget that moment as long as I live.

"Anyway, we luck out because instead of kicking us back out into the street, the bartender calls the cops and the cops get us on the train heading back north where we belong."

Dayla hadn't moved the entire time he was telling this story, but Will's cock never went soft. "What did you tell the cops? Did you tell them why you were down there?"

"Hell no. We told them we misread the Sox schedule, that we were going to a ballgame and got off at the wrong station. The whole episode changed my mind about paying for sex, I stayed a virgin until the night of the senior prom and I never paid for sex in my life; well, not directly anyway."

Will started to buck his hips and Dayla got the message. She rode Will to a wonderful mutual orgasm.

The next time they were together it was Will's turn. "What about you, Ms. Prichert. Tell me how you lost your virginity and all the kinky sex you've experienced."

Dayla laughed out loud. "You're going to think you're dating the biggest prude in Chicago. I've had sex with four men in my life."

Dayla laughed again when she saw the look on Will's face.

"The first man, really a boy, was a basketball player I dated for two years at the U. That's right, I was a twenty-year-old sophomore when Jason Gerry took my cherry. We'd been dating for almost six months when it happened after a night of drinking cheap wine. He didn't take advantage of me, the wine loosened me up enough to finally seduce him, he was always a gentleman and wouldn't dream of hurting me.

"I probably would have married Jason, but he died from a congenital heart condition. No one could understand how a college athlete could have a heart condition, he was in such beautiful shape, always running, always active."

Will saw the tears start to form in Dayla's eyes and he squeezed her shoulders. "Sorry I asked. You don't have to say any more if you don't want to."

"No, I'll be OK. I admit it still hurts when I think about Jason, he was such a nice guy and I did love him."

Dayla reached over to the nightstand and grabbed a tissue. She wiped her eyes and in the most unladylike manner, blew her nose. Dayla got up off the bed and walked naked into the bathroom, dropped the tissue into the bowl, flushed, and walked back to bed. Will watched her near-perfect form the entire time.

"OK, number two. That would be Jason's teammate, Tommy Rawlings. Almost a year after Jason died, Tommy and I started to date. Jason's teammates were always nice to me, before and especially after Jason's passing. Not one of them tried anything inappropriate, but slowly Tommy and I found a mutual attraction and began to go out without the others from our group of friends. A month later I ended up in Tommy's bed."

Will knew who Tommy Rawlings was, Rawlings spent two years in the NBA before blowing out a knee. He was 6'8" and black as coal. Will was having a hard time hiding the fear he was feeling. Dayla noticed it and smiled.

"Oh, I know what you're thinking. My girlfriends say you men are all the same. Of course, women aren't much different. I can't tell you how many of my friends wanted to know what it was like to be with Tommy, everyone assumes he's just as big down there as he is everywhere else.

"Poor Tommy. The myth of the black man's size is only a myth if Tommy is any indicator. Let's just say Tommy is very average in that department."

"Enough about that," Will replied while quietly sighing in relief, "what happened with you two?"

"His mom. She was kind of a bigot. Didn't want Tommy dating some white girl, especially after he signed his pro contract. Thought I was out to steal his money, which was a real joke since it was her that bled him dry when he only lasted a couple years in the NBA. You could see her in the stands wearing a ton of bling and screaming at the refs the few times he actually got to play."

"Sorry again. So, I'm assuming that leaves George."

"Yea, George. What a mistake that was. Within a few months of my promotion to head teller George starts wooing me. It wasn't harassment, I was a willing participant to the affair. He came from a wealthy family and did have some high-class charms. I was a twenty-five year old who hadn't had a serious relationship, and hadn't been laid, in two years; I was ripe for the pickings.

"You asked me once where I learned how to squeeze you like I do, you can blame Phoebe, you met her that first night at the tavern, the gorgeous black lady. When I complained to her about not knowing when George was in me, Phoebe said I should practice Kegels, she said it was the cure for pencil-dicked boys. I guess you're the happy recipient of all my exercises, not that you needed it any tighter with your size. But, I did need it with old pencil-dick.