Prudent Exchange

Bryce Finley and I (Kyle Worth) went to High School and college together, and in college were fraternity brothers. I was always the "Most Likely To Succeed," while Bryce was "Most Likely To End Up In Jail." One reason that I was voted "Most...Succeed" was because both in High School and college I ran businesses and actually employed classmates.

By the time that we were both 28 Bryce had two failed businesses and was on his third and almost went to jail for income tax evasion, but fortunately did avoid stir so he didn't live up to his "Most Likely..." moniker. I was grateful that I had lived up to my moniker and was a successful entrepreneur and the top volunteer fundraiser for the Police Boys & Girls Club in our metropolitan area.

I was in better physical shape than I had been in High School or college while Bryce was -- well, let's just say he wasn't.

Bryce did have something over me; he was married to Gail Finley nee Preston.

Gail is a perfect example of guys having different tastes in women. Gail is short, thin, with an A cup, and average hair. She does have a pretty face, but other women with faces just as pretty don't turn me on much. Her eyes are exceptional and she has the ability when she looks at you to cause you to believe that she's looking into your soul. Anyway, whatever the reason -- it may even be pheromones for all that I know -- I am hopelessly enamored with Gail. At the time that I was 28:

I would walk over hot goals to get to suck Gail's nipples.

I would fight an alligator to get to suck and lick Gail's clitoris.

I would trade a year of my life to get to fuck Gail.

Pathetic, right; especially since I'm married to Evelyn, who well more than 50% of guys would probably think is sexier than Gail. Also Evelyn is sweet, nice to everyone, and is smart and personable. We never fight and have a relationship of mutual respect.

************

For my story to make any sense I need to go into the history of my relationship with Evelyn, and she with Bryce.

Evelyn was from a poor family, and was able to attend college only because she had a full need scholarship. However, even that left her with no money for things that room and board and tuition didn't cover. Early my freshman year I put up an advertisement for my college business at the Student Center and she was one of the first people to apply.

Evelyn is really good looking and personable, although at least at that time she lacked self-confidence. It was a no-brainer to hire her. She was an excellent employee who worked ten-fifteen hours a week. I paid well enough so that gave her all of the spending money that she needed, although still not enough to go home on Holidays.

I don't really know how Bryce got into the college we attended. I know that his grades and board scores probably weren't up to snuff, but he did have some relatives who were alumni, and he is very personable and probably made an excellent impression in an interview, so maybe that was it. Anyway, he was industrious enough to just scrape by.

Bryce met Evelyn through me at the start of our sophomore years. They seemed to hit it off and started dating shortly after they met. By the start of their junior years they seemed to be inseparable and heading toward marriage after college. Then, near the end of their junior years they broke up.

At the time I was not sure exactly why they broke up. Bryce and Evelyn both changed their stories about it several times. The story that I ultimately chose to believe was that since Bryce was on academic probation Evelyn was afraid that he would flunk out, or if he didn't he'd never make it in business, and given her background of poverty she needed to avoid that with a passion.

Although I believe that it was Evelyn's choice to break up, that didn't mean that she didn't take it hard. She was a good friend of mine, not just an employee, and I gave her a male shoulder to cry on. While I empathetically listened to all of her troubles the one that hit me the hardest was that her parents had been evicted from their apartment and she had no home to go to over the summer, and the job she thought that she had in her home town fell through. I became her white knight.

"Evelyn, in the summer I really ramp up my business, and I need a full time employee. Why don't you work for me full time this summer?"

Evelyn wasn't as taken aback by my suggestion as I might have thought, which led me to believe she was hoping that I'd ask her. After a pause she said "But I don't have any place to live."

"Let me call my parents," I said. "They have a big house and my twin brothers are graduating college and at least one of them already has a job in another city, so we would have room."

"Do you mean it?" she asked, on the verge of tears.

"Let me inquire; I can't promise anything, but I don't see why not."

"Uh...you're not expecting me to...uh...I'm embarrassed to ask this...uh...sleep with you, are you?" she stammered.

I chuckled. "My parents are overly religious and strict, and even though I do not share their outlook on life I can assure you that the possibility of us 'sleeping' together in their house is between none and slim, and Slim just left town."

I called my mother up that same night, she got dad on the phone with her, I told her about Evelyn's situation, and once I assured them that we were not romantically or sexually involved (I told them both terms; even though they didn't distinguish between them, I did) they were on board. "I've always wanted a female around to discuss girl stuff with," was my mother's parting quip.

Evelyn was a great employee, good enough so that I ended up paying her per hour twice what I paid the three other summer employees I had (all part-time). Her extra pay also because I knew that she really needed the money for school and was sending some to her still homeless parents. My mother absolutely loved having Evelyn around and took her out shopping enough so that by the time that school was about to start up her wardrobe was ten times as nice, and extensive, as it used to be. At first Evelyn was embarrassed by my mother's largess but when I pointed out to her how happy it made my mother, and how easily my parents could afford it, she humbly accepted the clothing.

At school I had dated pretty extensively, but had no steady girlfriend. At home during the summer I did go out on a few dates, but since I felt bad about leaving Evelyn at home since she didn't know anybody in my home town (except Bryce, who she was avoiding) and didn't have transportation, I usually took her along to outings and parties. Because of how good-looking and nice she is she was often hit on, but so politely as to almost be obeisant turned away all comers.

Evelyn and I really liked each other but there didn't seem to be a romance spark despite the fact that we were together all summer. After the first month it was apparent to me that my mother would be very happy if we ended up in a romantic relationship -- as long as there was no sex before marriage (lol).

Things took a turn the last weekend before we were to return to school (on the coming Thursday). My parents were helping my one older twin brother who had been living with us that summer, but had now gotten a job out-of-state, move. Evelyn and I were alone for the first time that Friday night, and would be through Sunday night.

The previous Wednesday Evelyn had gone to a doctor's appointment; I let her use my car. She never said what it was about, and I never asked. That Friday night we ordered in Chinese and Evelyn was more insistent than I had ever seen her that we watch a DVD that she had purchased. I was cool with it since I wasn't really keen on going out anyway.

After we took a walk in the neighborhood to digest our food we sat in our parent's in-home theater (like I said, they're wealthy) and Evelyn put the DVD in and sat next to me, leaning her head against my shoulder even though we were in theater seats. I didn't recognize it until we were about twenty minutes into the movie that it was soft porn. I gulped when the first vivid sex scene came on, and had unwelcome activity at my crotch. Despite the fact that it was fairly dark in the room Evelyn noticed. How do I know that she noticed? -- because she rubbed her hand over my tented crotch.

When I looked at Evelyn with must have been an expression that was probably somewhere between surprise, bewilderment, and lust, she kissed me lightly on the lips and staring into my eyes said "You were never going to make the first move, so I will."

With that she stood up, started stripping somewhat in sync with the music from the movie, and once she was naked stood me up.

Her premeditation -- if I had any doubt that that was what it was -- was confirmed when suddenly two exercise mats were extracted from the second row of seats and placed on the floor, and then she moved my hands to her boobs and started passionately kissing me.

As earlier indicated, Evelyn is a very attractive woman, both in looks and personality, so I quickly disrobed. Soon we were prone on the mats mauling each other. After a few minutes of that she moaned "Fuck me; please fuck me."

"I...I...don't have a condom," I stuttered.

"I got my Depo-Provera shot Wednesday, and you know that we're STD clear," she mumbled, as she grabbed my cock and moved it to her vaginal vestibule.

Our first fuck was sweet; really, really sweet. Despite our apparent lust we were measured in our mating, not animalistic. Our orgasms were virtually simultaneous, extended, and serene. When we regained our wits we went up to my bedroom and spent the rest of the weekend getting as well acquainted sexually as we were in normal life.

When we got back to school we were boyfriend and girlfriend. The first quarter Evelyn had to live in the dorm since that was necessary for her room and board although she spent many nights at my off-campus apartment. After the first quarter she was able to finagle some sort of payment in place of her dorm room and board and she moved in with me.

Because I was always straight with my parents -- even though I was already financially well emancipated from them -- I called them up the first weekend that Evelyn was living with me. If she hadn't lived with my parents the previous summer there likely would have been tears, accusations, gnashing of teeth, and some form or another of retribution, but since my dad really liked Evelyn, and my mom had bonded with her (and talked to her on the phone once every three or four days after we got back to school), there was virtually no acrimony. My mother's only concern "I hope that you'll do the right thing and marry her, Kyle." By that time I was thinking the same thing.

Evelyn and I got married two months after we graduated. Per my instructions my parents made it as simple as my mother was capable of making it. Once we had announced our engagement half way through our senior year my father got Evelyn's parents jobs and got them into a rent controlled apartment and my parents paid for them to attend the wedding, properly clothed. They were very happy that their little girl -- their only child -- had escaped poverty.

Bryce was one of the groomsmen at our wedding. He and Evelyn were still friendly with each other, and Bryce had never begrudged her ending up with me.

Obviously Evelyn never worked for me after we got engaged, but after the honeymoon she got a job that took advantage of the skills she had learned working for me and considering how smart and personable she is was definitely going to succeed. I started another company, after selling my college one for six figures, and also was definitely going to be successful.

Evelyn and I had enough money from my previous companies to buy a decent house just before we married. Bryce rented a condo in the same metro area, about three miles from our house.

Bryce met Gail about a year after Evelyn and I got married. I'm not even sure how they met but Gail is a year older than Bryce and I, and she had a decent job in sales, which I believe she was very good at. They seemed to really hit it off and were married about six months after they met. Evelyn and I were both in the wedding party since Gail and Evelyn seemed to have also really hit it off.

*************

Getting back to my story after the history lesson, Evelyn and I were both 28 and had been married going on six years when I was sitting in my office reviewing a prospectus for a company that was on the market for purchase when my secretary Cher rang. "Bryce Finley here to see you," she chimed.

I knew damn well that Bryce didn't have an appointment, but since he was a long-time friend and the prospectus could wait I told her "Send him in Cher."

Bryce entered with a big grin on his face. "Hope that I'm not interrupting anything but I've meant to see you for a while and I was driving by so I thought that I'd stop in."

"No problem," I smiled as I shook his hand.

We made small talk for a while and then Bryce sighed and said "The reason that I'm here is because I need a loan. My business is starting to really get going but I've got a cash crunch. If I could just borrow $45,000 for a year I know that I could get over the hump."

The $45,000 didn't really mean that much to me, but losing Bryce's friendship -- and maybe not getting to see Gail again -- would be a loss. Loaning money to friends -- especially someone like Bryce who already had two failed businesses -- was the surest way to end a friendship.

I tried to let Bryce down gently -- including by telling him the truism about losing friendships when money is lent -- but he was insistent and I actually saw tears starting to form in his eyes. Finally, I broke down and said "OK -- provide me with your latest financial statement and a one page memo about what the money will be used for and how that will help turn things around and I'll carefully consider it."

"Can I email the stuff to you today?" he asked. "I'd...I'd...uh...I'd really like to get the loan by Monday of next week."

"Sure," I smiled. We shook hands, and he left.

I got his email within ninety minutes. I looked it over, and as I expected he didn't know what the hell he was doing. I wondered how he could have a business degree and still be so unsophisticated. I had a lot to think about, though, so I called him and told him that I'd give him an answer by Monday, and if I was agreeable would have the check messengered to him then.

That Saturday Evelyn and I went to a pool party that some friends of ours (the Jepsons) were hosting at their mini-mansion in a remote suburb. By the time that we were driving there I was sure that I would be turning Bryce down, I just didn't know how to sugar coat it.

Imagine my surprise when we got to the party and Gail was there. It turns out that she had gone to college with our hostess Sheri Jepson. Although Gail is far from voluptuous when I saw her in a bikini I instantly tented my pants, especially overcome by her perfect thigs and ass. I was extremely embarrassed by my instinctive reaction, especially since I couldn't properly evaluate why I always had the reaction to her that I did.

After I regained my composure, and suppressed my wayward cock, I saw Gail terminating a conversation and approached her in as friendly a manner as I could. I usually was almost tongue-tied around her, but for some reason I wasn't that afternoon. "Hi Gail," was my stellar greeting, followed by a hug that I tried to keep as innocuous as possible.

"Hi Kyle," she seemed to genuinely smile, while returning my hug, much less cautiously than the one that I was giving her. "Where's Evelyn?"

"Evelyn is talking to Sheri Jepson, I'm sure that she'll be around soon. Is Bryce here?" I replied.

"No," she frowned, "he's trying to put fires out at work this weekend. I'm a little concerned for him. He's been under so much stress about his business lately, including saying that we may have to move from our rented condo. But, no downers today -- let's have fun. Why don't you get into your suit and we can do some laps in the Jepson's pool. I've always heard great things about saltwater half Olympic sized Infiniti pools and I've never seen one before, and no one else is in it yet so we can christen it."

You bet your sweet ass that I was changed in 60 seconds flat, and we dove in together. We leisurely swam six laps, chatting as we did so, and then she challenged me to a race. I probably wouldn't have beaten her anyway since my muscles are designed for lifting weights and rnning, not swimming, but I did ease up at the end to make sure that she won so that I could compliment her without feeling too much like a pervert.

At the party I had more one-on-one time with Gail than any other time in my life up to that point. It was probably -- counting when we were in small groups (which I still considered one-on-one, including with Evelyn who greeted Gail warmly) -- more two hours of time together. I didn't ignore Evelyn and she seemed to be having a good time without constant attention from me.

Gail had come with someone who wanted to leave early but I asked her to wait until I talked to Evelyn. In my sweetest manner I asked Evelyn if we could give Gail a ride home, and she was happily on board. That gave me even more time with Gail during the fifty minute drive to her condo (about three miles from our house). Gail -- sitting in back -- and Evelyn had a good chat during the ride, and as always when they got together seemed to get along great. I had to keep checking my rearview mirror -- I didn't want any spy vehicles trailing us (lol) -- until I noticed my traitorous cock acting up again so then I had to keep my eyes straight ahead.

After spending a good part of the day with Gail when I got Evelyn home she didn't have a chance if she wanted to avoid getting ravished. As she exited the shower with a towel wrapped around her I was standing there naked with my cock at full salute and a wicked grin on my face. "What are you leering at, pervert?" Evelyn asked with a mild grin on her face.

"I'm looking at who I wanted to fuck the entire day, but couldn't in polite company. You looked so hot in your bikini I almost did you on the pool deck," I snarled while maintaining my diabolical grin.

"I thought that you were ogling Gail Finley," she said, in a tone that was hard to decipher. She may have been serious, maybe provocative. I didn't care which.

"After the next hour you tell me who I wanted to ravish in the Jepson's pool, bitch," I snarled some more as I approached her and ripped her towel off of her body.

Evelyn shrieked.

I picked her up and threw her over my shoulder, caveman style.

She pounded on my back saying "Release me you animal."

I bounced her on the bed and before she could escape I pounced on her, held her arms above her head with one of my hands, and with the other hand started playing with her pussy.

"You're an animal, a fucking animal," she groaned, maybe half-seriously, but certainly not fully serious.

"I'm not a 'fucking' animal yet, but soon I will be stroking in your sweet pussy," I growled.

Then I started sucking her tits, one and then the other, as my pussy hand kept up the stimulation. When she had her first orgasm from a combination of my hand on her pussy and my mouth on her nipples I let go of her arms, positioned myself above her with my lips on hers and my hands on her prodigious boobs, and then slowly but purposefully ran my snake into her chasm. When I bottomed out she groaned into my mouth.

Evelyn does have a sweet pussy. She also has nice thighs that she wrapped around me. Her tits are more than stimulating. However, it was none of those that caused me to have the most intense orgasm of my life as I stroked in-and-out of her cooch. What caused me to have the most extreme orgasm of my life was imagining that it was Gail that I was laying pipe in.