Rob and Gail

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Saturday I went to the gallery, paid for the painting and then paid extra to have the painting packaged and shipped to Gail. I hoped that she would think of me every time she looked at it and wonder about what could have been.

Thursday I walked across the stage, received my sheepskin and headed into the next portion of my life. My parent's graduation present to me was a one year lease on a two bedroom condo and the furniture to fill it. I spent the weekend moving in and on Monday I started my full time job in the family business.

I'd worked there summers since I was fourteen so there wasn't any 'new guy' break in period. I already knew the people that I would be working with so I was able to hit the ground running. And speaking of running; I'd never stopped since Mike got me started. I ran nearly every morning and I was in the best physical shape of my life. I knew that sitting behind a desk all day wasn't going to help me stay in that shape and that just running wasn't going to be enough.

There was a gym two blocks from the office and I joined and started working out on my lunch hours on Monday, Wednesday and Friday. Turns out that one hour just wasn't enough time for a work out when you subtracted the time it took to get there, the time it took to shower after the work out and the time it took to get back to the office so I started going in at five in the morning when they opened. It worked out so well for me that I started going in every morning.

The gym also had classes during the day and in the evenings for everything from spinning to tai chi chuan and I decided to take the class on tai chi two nights a week when I got off work.

+++++++++++++++++++++

The Fates or whatever Gods that be must get some sort of perverse pleasure out of fucking over mere mortals like me.

It was the third week since I started the tai chi class and I got to the gym at my normal time and on the way to the men's locker room I had to pass by the circuit machine and free weights area. I happened to glance in and saw Gail working out on the seated leg press. She saw me and I looked away from her and hurried to the locker room.

That night's tai chi class was wasted on me. Tai chi is all about concentrating on your inner core and I could not concentrate for shit. As hard as it was to do I'd thought I had made some progress on putting Gail behind me and now here she was back in the forefront of my mind. Luckily she was gone when I got out of class and I didn't have to try and avoid her.

On my way home I wondered if I was going to have to drop the class to keep from having to see there which was a one hundred and eighty degree change from when I was in school and did everything in my power to be where I could see her. The difference of course was that back then I had hope. However thin it was it was still hope, but she had crushed that hope on our last date.

The Fates and the Gods were not done with me yet.

The next day at work I was in my office reviewing contracts when Marva, the secretary I shared with three others, called me on the inter-com and told me that there was some one from Ferris Industries there to see me. I was expecting a contract from Ferris and I had thought it was going to be sent over by messenger, but I guess that John over at Ferris thought that it was important enough to be hand delivered. I told Marva to send the visitor in.

The door opened and I moaned, "Fuck me."

"I'd love to" Gail said as she walked into my office. "May I sit down?"

"Please do" I said.

"First off" Gail said, "I had no idea I would be delivering this contract to you" she said as she handed me the envelope. "I didn't even know that you worked here. But I'm glad because now I can thank you for the painting you sent me. I didn't even realize that you knew I liked it. I do have a question for you though. How did you find out I worked at the gym?"

"I didn't know. I work out there every morning and I only started taking the evening tai chi class a few weeks ago."

"Why am I having a hard time believing that?"

"Maybe because you don't want to believe it."

"Why would I not want to believe it?"

"Maybe you got used to me being close by and it bothers you that I haven't been since graduation. Maybe you don't want to believe it because you are wishing that I would be around. I don't know if either of those is true or not, but you can check with Nancy, the morning girl behind the entry desk, and she can tell you when I joined and when I come in to work out."

"You might be right. Maybe I'm having a hard time believing that some one so desperate to just see me that he hung around every place he thought I would be could just quit and disappear."

"Quit and disappear? Have you forgotten our last date? You did the verbal equivalent of kicking me in the balls. Of course I got the message. The night you dropped me like a hot rock added to what you laid on me on our last date came through loud and clear. Believe me lady; if I had known that you worked out at that gym I never would have joined."

"That from a guy so desperate to see me that he became my shadow?"

"No. That from a guy who could not bear to look at you knowing that there was absolutely no hope for him. It was one thing when there was a smidgen of hope. It was something else again to know that there was absolutely none."

"You would have rather I'd said nothing so you could go on wasting your time?"

I just shrugged and said, "Thank you for bringing the contract. Tell Mr. Stiles I'll review it and get back to him sometime tomorrow afternoon."

Gail sat there and looked at me for several seconds and then she got up and left.

"Why me God" I said to myself as the door closed behind her. "Why don't you go and fuck with someone else."

++++++++++++++++++++++

My friendship with Mike had continued after graduation and I had dinner with him that evening after work.

"You seem down" he said as I picked away at my meal.

"I had a bummer of a day."

"Hey dude, it is only work. You get to walk away from it at five o'clock."

"It wasn't work. Gail stopped in at the office today. I was making progress at getting over her and then there she was sitting across from me in my office."

"I'm sorry Rob."

"What do you have to be sorry for?"

"For getting you mixed up with her."

"What do you mean by that?"

"Nothing bud."

"Oh no you don't Mike. You can't say that and expect me to just let it pass. What did you mean when you said you were sorry for getting me mixed up with her?"

He was silent and I said, "Come on Mike; spit it out."

He shrugged and then said, "You know I'm a horn dog and a bit of an asshole where girls are concerned right?"

I nodded a yes.

"The reason I went through so many girls had nothing to do with my manly charm. To put it bluntly I'm rather well hung. I didn't have to chase the girls. Mostly they chased me. I guess girls talk among themselves the same as guys do. Anyway, the word spread about my package and girls would come up to me and ask if it was true and my response was always "There is only one way you will find out" and four out of every five said "Lets get to it."

"Gail was one of the girls who came to me and asked the question. I knew you were hung up on her and you had already told me about the first time she had talked to you so instead of giving her my standard response I told her the only way she would ever find out was if she did me a favor and cut you a break."

"Cut me a break?"

"Yeah. Talk to you. Be civil and like that."

"So after she made nice with me she came back to you and sampled the goods?"

"No bud; I'm an asshole, but not that big of an asshole. I screw the babes, not my buds. She did come back though, but only to cuss me out."

"For what?"

"Messing with her mind. She said I'd set her up with a good guy even though I knew it wouldn't go anywhere. She was really pissed when she told me that and I didn't have a clue as to what she was talking about."

"I guess that explains it. I wondered at her sudden turn around. Now I know."

Suddenly it dawned on me that Gail wasn't the first one Mike had sent my way. I remembered back to when girls started coming up to me in the cafeteria and asking if they could join me. I didn't know if I should scream at Mike for helping fuck my life up or thank him for making it possible for getting what little I did get.

++++++++++++++++++

The next trick the Fates and the Gods played on me was the next morning. I showed up at the gym at ten to five and I was standing there waiting for Nancy to open the door when a voice behind me said:

"Good morning."

I turned and saw Gail standing there.

"I decided that early mornings would work better for me."

"I don't believe it. I think you just want to torment me."

Before she could reply Nancy opened the doors and we followed her to the front desk. "Decided to bring your wife with you" Nancy asked.

Gail laughed and said, "He wishes."

I said nothing and just swiped my membership card through the card reader and headed for the men's locker room. I had no idea what Gail's program was, but I hoped that she worked the circuit machines first. That way I could avoid her because I usually started with cardio on the treadmill which was at the other end of the building from the circuit and free weight area.

Naturally I didn't get what I wanted. There were five treadmills in the cardio section and Gail was on the one in the center which meant that no matter which of the other four I chose Gail was going to be almost right next to me. I could have just turned and gone to the circuit area, but why? I needed to face up to the fact that if Gail was going to be around the only way to avoid her would be to quit working out at the gym and find another one.

But who did I think I was kidding. Certainly not myself. Yes, I had started trying to put Gail behind me after graduation, but she was still there in my mind and I thought of her often. I was able to survive her dropping me and still go where I could manage to see her and now here she was only eight feet away. I knew that nothing would come of it, but she was where I could be around her now so I was going to take the gift that the Fates and the Gods had given me.

I did my usual fifteen minutes on the treadmill and then moved to the circuit area to begin the rest of my workout. I was not at all surprised when a couple of minutes later Gail showed up. We hadn't said a word to each other when we were on the treadmills and we didn't talk as we worked our way through the fourteen machines. Didn't talk, but I watched her and she knew I didn't take my eyes off of her.

When I finished my routine I headed for the locker room and changed into my swimming trunks and went to the steam room where I spent just over eight minutes before heading for the hot tub. I'd no sooner sat down in the 105 degree water when Gail showed up and joined me in the tub. She was wearing a bikini and seeing her in it gave me instant wood. Fortunately with all the bubbles and the swirling water Gail couldn't see it, but I would have been willing to bet big money that she knew it was there.

"We seemed destined to run into each other" she said.

I could have just shrugged and kept my mouth shut, but I decided that sticking my head in the sand and pretending that she wasn't there would be a waste of time since she knew that I was hung up on her so I said:

"I'm not going to complain, but couldn't you at least toned down the impact by wearing a tank suit instead of that bikini?"

"Tone it down? Why would I do that? This suit was designed to get attention and that is why I wear it."

"I thought that you didn't want my attention. At least that was the impression I got when you stopped dating me."

She was silent for a few seconds and then in a soft voice said:

"Things change."

"In what way?"

"I told you on our last date that my feelings for you were getting stronger than just like and I guess that they were stronger than I realized. I've not gone a day since that last date that I haven't thought of you. It was a happy surprise to find out that we belong to the same gym, but it wasn't by accident that I delivered that contract to you. I knew you worked there and when my boss told me to call the messenger service to send over the contract I told him I knew you and that I would like to bring it over so I could say hi."

"Why?"

"To put myself in a place where communication could happen."

"Again, why?"

"Do I have to carve it into your chest?! I've missed you dummy! That's why!"

"I've missed you too, but nothing has changed. I still intend to keep my promise to my mother."

"I admit that is a problem, but maybe we can work around it."

"How do we do that?"

"We will think of something. So! Do you ask me or do I have to ask you?"

"Ask what?"

"For a date you blockhead!"

"A date? You and me?"

"No. Me and your mother. Of course you and me."

I have to admit that I was surprised and I just sat there and looked at her as I tried to process what had just happened. I don't know how she took my silence, but apparently she thought I wasn't going to ask her so she said:

"Okay. I'll do it. Would you like to have dinner with me tonight?"

I might have been sitting there confused, but I'm not a complete dummy so I answered:

"Of course I would."

"Pick me up at six?"

"I'll be there."

+++++++++++++++++++++++

I rang her doorbell right at six and when she opened the door she took my breath away the same as she did the first time I'd picked her up. I remembered how much she had enjoyed the Veal Marcella at Tricocci's so that is where I took her.

Over dinner we talked about adjusting to life after sixteen years of school. She had decided against going for an MBA and she liked her job and was looking for a place of her own. I was almost tempted to tell her she could move into my spare bedroom, but I didn't because I was afraid she would think I was pushing too hard and it might push her away and that is the last thing I wanted to happen.

We had both turned twenty-one since our last date and so I took her to The Pit for drinks and dancing. God but did I ever like the feel of her in my arms and her body pressing against mine had predictable results and she felt it, smiled and said:

"I don't think your mother would approve of that."

I wisely did not respond to that.

We left the lounge around ten-thirty and she had me pull over and park a block from her house. She slid over next to me and said "Kiss me" and I did. I did for the next twenty minutes. When I walked her to her door she kissed me again and said:

"I have something I need to do tomorrow, but I'm free the rest of the week."

"Day after tomorrow?"

"You have a date" and she kissed me again.

++++++++++++++++++

By the end of our fourth date we were back to finger fucking and hand jobs. It was on our tenth date and I was parked the usual block from her house when she asked me:

"How do you interpret virginity?"

"I beg your pardon?"

"Easy enough question sugar. How do you define virginity?"

The question stumped me because I'd never given any thought to it.

"Let me help you out a little bit. You don't seem to mind playing with my pussy and you haven't shoved my hands away when I give you hand jobs. Do you see putting your dick into my pussy as the only way to lose your cherry?"

"I've never thought on it."

"Then let me ask you this. Would my giving you a blow job be any different than my giving you a hand job?"

I thought for a minute and then said, "I don't honestly know. I guess I've always assumed that making love for the first time is when you give up your virginity."

"That's the way I see it too. I've already told you about my high sex drive and that I can't go without sex for as long as it would take my mother to plan the wedding. I think I can get by if you eat my pussy. If you will do that I will of course suck your dick. It is the orgasms that I get from having sex that drive me. If you can give me those orgasms by eating me I should be okay. What do you think?"

"I don't know. I've only done it a couple of times so I don't really know how good I'd be at it."

"I can teach you how sugar. It isn't a hard thing to do. Want to give it a try?"

I thought about it for a bit and then said, "I'm willing to try."

"Tonight?"

My answer was to start the truck and drive past her house as I headed for my condo. I had never mentioned my condo to Gail so she was surprised when we got there.

"I thought you still lived at home at that we were on our way to a motel."

"Mom and dad kicked me out. This is their bribe to get me to leave without a fuss."

Once inside she looked around and then said, "That painting that you gave me would look just right on that wall" and she pointed at the east wall of the living room. I'd been meaning to get some art work for the walls and so I said:

"Maybe, but it is your picture so if I was to put it on that wall you would have to come with it."

"It could happen sugar, but a few things have to happen first."

"Like what?"

"Let's count them off. First a proposal and a ring. Next we tell my mom so she can get started on the wedding she has been expecting to give me since I was sixteen. There is one other thing that comes between the proposal and us telling my mom but I will leave it for later."

"Why?"

"Because I need to lock you in and make sure that we are firmly attached before bringing it up. Now, would you care to sit down on the couch with me and neck until we get hot enough to do what we came here for?"

I found out that I enjoy the hell out of blow jobs and I also found out that Gail thinks I have talent when it comes to eating pussy. Following her instructions I was able to get her off. Twice!

Following that night we saw each other three or four times a week and after a month and a half of joint oral sex I bowed to the inevitable and bought a ring.

We were at my condo following and evening of dinner, drinks and dancing I took a knee and asked the question.

I did not get the response I expected.

"I would love to sugar. I would love to and I really do want to, but I have a condition and I don't know if you will be willing to meet it."

"We won't know until you tell me what it is."

"Remember way back when I told you that I couldn't go a week without sex? Well that hasn't changed any. I thought that the orgasms from oral would hold me, but they haven't."

"But..."

"Let me finish sugar. I need to get this out into the open. I want you. I really do want to be your wife, but you are holding steadfast to the promise you made your mom. That by the way is one of the things I love about you. The fact that you have integrity. But it is also a curse because it keeps you from giving me the sex I need. I'm not lying when I say that it will probably take my mom six months to plan and put the wedding together and I can not go six months without sex. You are fantastic when it comes to eating my pussy, but it isn't enough to hold me.

"There are some things I will not do and cheating is one of them. My seeing other guys and having sex with them is not cheating because, at least not yet, you and I are not in a committed relationship so my seeing others is not cheating on you. At least it isn't as far as I'm concerned. If I say yes and accept your ring and still saw other guys for the sex I need it would be cheating. It would be cheating unless you were okay with it. If I say yes you would have to be okay with me seeing someone else once or twice a week until we could consummate our marriage and I honestly do not think that you can do that."

"You mean you have been making love with other guys all the time we have been dating?"