Never Bet with your Heart Ch. 01bymonkeytail10103©
My wife Jill and I moved from North Carolina to New York City after I got a promotion with the investment group I worked with. We hated to leave our home state but it was a good opportunity and since we were in our late 20's and didn't want to start a family for a few more years we thought it would be fun to live in the city for a couple years and hopefully we could return back to our roots in a few years. We did love the city but found very quickly that despite my promotion and increase in pay it didn't go far there. We opted for a small place in the city so we could be in the middle of the action. It was cramped but we managed.
Things were going good and I was adjusting to the faster pace of the big city. My wife was getting bored during the days while I worked so she got a retail job just to occupy her time and to make a little money on the side. It was summer time so we often went to the park or caught a baseball game in one of the cheap seats as we were both big sports fans, my wife actually even more than me.
At work my direct report was a good guy, about 10 years older than me I figured. His name was Ty, a black guy, about 6-2 and pretty-good looking from a male's perspective. I had heard rumblings from a few co-workers that they didn't think he had put in his dues to have his job but from what I had seen so far he fit the bill for what I would have expected, age aside. He was very polished, dressed immaculately and was a good communicator and clients loved him – exactly what team leads seemed to be these days. I was happy he seemed to take a liking to me as well as that could only help my future. Via some small talk one day he found out I had gone to North Carolina for college, as did my wife, and he informed me that he went to Duke where he played football. That was a strike against him for sure but we laughed about our mutual hatred for the other school. But he said he loved his time in North Carolina and spent most of his social hours on our campus instead of his. I knew why – Carolina girls were gorgeous and Duke was not known to have the hot co-eds – which he readily acknowledged. He asked how my wife and I were adjusting to the city and I said things were going okay but that we were finding it expensive to really get out and do anything. He agreed it could get pricey out there.
A few weeks later Ty had several members of our team over to his place on a Saturday for a team-bonding type event. We were encouraged to bring spouses and kids and most people did. We dressed casual, me in a golf shirt and shorts and my wife in a nice sundress. She looked great I thought, and usually did. She was 5-2, 110 with mid-back length blonde hair and a very athletic figure. She usually drew her share of looks. When we got to Ty's we were immediately taken by it. He had an incredible apartment that was about 50 stories high and had wall-to-wall windows that overlooked the park and a patio that wasn't big but that allowed for a small group of people to hang outside as well. I introduced Ty to my wife and he was very gracious and welcomed her to his place and the city. We small talked for a bit and he made his way around making sure he talked to everyone.
As I talked to other team members they all felt he was showing off his digs and life to everyone and rubbing it in their face. Apparently he came from some money and his father was a successful real estate owner in the city and that is how he had this apartment. Maybe it was because I was new but I never sensed anything about Ty that others did. I chalked it up to jealousy.
My wife and I had made our way to the patio when Ty came out and said to my wife that he heard she was a big sports fan to which she nodded she was. She responded that I had told her he went to Duke and played football and she started to give him crap about it. He took it in stride as she teased him for Duke not winning many football games. He laughed and said that they definitely took their share of beatings, especially while he was there. The teasing was all good-natured and we shared several laughs. My wife was pretty competitive and she really hated Duke so I was impressed that she didn't let her true hatred shine through since this was my boss after all. When we were about to leave Ty called us over and said he had 2 tickets behind the plate for the Yankees game the next afternoon and that if we wanted them we were welcome to have them. We were thrilled and accepted as usually we sat in the nose bleeds. We thanked him and my wife gave him a hug and we headed home.
We had a great time at the game and I sent Ty a picture of us from my phone with the game in the background saying thanks and that we really appreciated the tickets. On Monday I thanked him again and brought in some cookies that Jill baked for him as a thank you. He said he was glad we had a good time and seemed genuinely appreciative of how thankful we were.
Over the next couple weeks I went to lunch with Ty a few times at his invite. He confided that he didn't think a lot of people on the team liked him that much and I told him I thought they were jealous of his success. He said maybe but that he had earned everything he had gotten at work. From what I had seen of his work to that point I agreed.
From that point on we became pretty good friends and my wife and I would go out with him socially from time to time and we always enjoyed his company. Ty was single, never married, and when my wife finally got him to open up as to why he told her he had been engaged to someone and then it fell apart and he just hadn't felt like going through that again. He pulled out his phone and showed us a picture of her and she was stunning, looked like a slightly older version of my wife I thought just as my wife said out loud that she could pass as her sister. I guess the fact that she was white never even fazed us.
As college football season heated up my wife and I liked to go to a pub or sports bar and have a few drinks and watch the games. Like I said, she loved sports, and it was also a way to get out of our cramped space for the day and not spend a fortune. Ty joined us a few Saturdays when he was available and he was always impressed with my wife's knowledge of the game. As we all sat and watched games my wife reminded him that the Carolina-Duke game was next week and that it wasn't going to be pretty. He laughed and said you never know and that is why they play the game and that he liked Duke's chances this year. My wife asked if he wanted to put a friendly wager on it and he said he wasn't a fool and that since Carolina was favored to win the odds were stacked against him. My wife had a quick solution. We'd make a bet on the football and then both of the two basketball games between the schools later in the year. Since basketball was much more even Ty agreed.
As we tried to figure out a good bet nothing really seemed to work. For Ty, nothing monetary would work as he had all he needed. We decided we'd all think over the week and decide before the game started the next Saturday. All my wife and I could come up with was along the line of sports tickets that Ty seemed to have access to but baseball was now over, maybe he could get some good Knicks tickets or something. We decided we'd see if Ty came up with something. When we met up on Saturday we asked Ty if he had an idea. He said he did and we were all ears. He said if Carolina won he would call in a favor to someone he knew at the Park Hotel and get us a comped night in one of their suites that overlooked the park. My wife about jumped out of her seat with excitement. She said yes without even looking at me or waiting for his side of the bet. And if Duke wins I asked? He said if Duke wins, then he wanted to take pictures of Jill wearing various Duke attire and keep them as souvenirs.
She laughed and said, "You mean like wearing a Duke shirt or something?"
Ty replied, "Yes" but that he would order several things with Duke logos and enjoy making he wear them.
My wife agreed and said, "That doesn't seem like an even bet but if that's what you want I can do that. Besides Carolina will win."
So the bet was agreed to. Carolina led most of the game and my wife was enjoying and gloating a bit too much for my tastes as I knew games could turn on a dime. She kept saying how much fun the Park Hotel would be and that she wanted to get pampered and bounce around in the big bed. She had a smile a mile wide. Duke cut the lead to 6 late in the game and Carolina really only needed one first down to run out the clock. Of course they didn't get it and Duke got the ball with one last shot. And of course they scored to tie it with 11 seconds left. It was all up to the extra point and we needed overtime to have any chance. My wife hadn't opened her mouth at all in the last ten minutes other than to cuss. The kick was good and after a last ditch Hail Mary the game was over.
Ty just smiled as I shook my head and Jill put her head in her hands. She hated to lose. And she hated to lose a bet even more. But she was a pretty good sport about it and Ty never rubbed it in. Before we left he said he'd order some items and we could come over next weekend to take the photos. Jill told him to go easy on her and gave him a hug and kiss good-bye as I shook his hand and said see you on Monday.
Jill complained all week about having to put a Duke outfit on and I was like it was no big deal it was just a logo. She agreed but said she hated Duke so much it seemed like a betrayal. The next Saturday we went over to Ty's place to pay up. He welcomed us in and we shot the breeze for awhile, had some snacks and a drink as we watched some football.
Finally my wife said, "Ok, let's get this over with."
Ty told her there were four outfits with instructions on his bed. She was to open one numbered box at a time and follow the instructions and come out and pose for us as he took a few of pictures of each outfit.
She let out a groan and playfully sulked back to his bedroom. Ty looked over at me and I just shook my head. It serves her right I told him. A few minutes later my wife came out decked out in a Duke cheerleader outfit, skirt, top, striped socks and pom-poms. She did not look happy and I laughed as I saw her and that made her laugh.
Ty said, "Finally I have seen a good looking Duke cheerleader" to which we all laughed as we knew that was true.
And my wife did look great. Ty got up and got his camera and took a number of photos with my wife posing and cheering for Duke. I had to admit she was being a good sport.
She went back for outfit #2 and returned with a low cut Duke t-shirt that really showed off her cleavage and tight little yoga pants. Again she looked hot and posed for her pictures and being a good sport. Outfit #3 had my eyes bugging out as she walked out of Ty's bedroom. She was wearing a Duke blue bikini that had the little devil logos on the triangles covering her boobs and a "D" in the middle of the bottoms. She also was wearing blue strapped high heels.
Ty said, "Now we're talking," as Jill walked out and I just stared at her.
She posed many times again and seemed to get into it. When she turned and looked back at us the look was so sexy my dick got hard and I realized almost her whole ass was exposed. Not a whole lot was said by any of us during these photos. Ty told her that was good and go back for the last box. He said that was the one she would like the most. When he said that I wondered what he could like more than that.
Then I heard Jill say from the bedroom. "I can't come out like this."
"A bet is a bet," replied Ty.
My jaw hit the floor as Jill came into view. She was wearing an almost sheer blue teddy that had "Go Duke" screened into it and was still wearing the high heels.
The words "Holy Shit" escaped my mouth and Jill smiled at me.
She seemed a bit embarrassed and was less forth coming in getting into poses.
Ty told her she had more clothes on now than with the bikini, which I guess was technically true. He reminded her that this was the last one and then she was all done. She sighed and then gave us some naughty looks as Ty snapped his pictures. I could see her erect nipples poking at the fabric and was losing my mind.
"Lift the teddy," said Ty.
My wife did and the tiny blue g-string again had that little blue devil barely covering her pussy.
I was rock hard as Ty said "Perfect" and snapped a few more pictures.
Ty then said, "Ok spin around and a few more pics and we're done."
When she spun around we basically were looking right at her bare ass as the g-string was swallowed by her perfect ass. I heard the camera click away as I tried to contain my thoughts.
Jill hurried back to the bedroom and changed back into her original outfit. She came out about ten minutes later looking a bit flushed over, no doubt from basically just exposing herself in front of us. We made some small talk and Ty said he would enjoy his souvenirs to which we all laughed.
When my wife and I got home we absolutely devoured each other. We had sex for several hours and I'm not sure either of us had ever been like that. Afterwards she said that she got so turned on during the photos that when she went back the last time she got on Ty's bed, pushed the g-string to the side and fingered herself to an orgasm. She said she was so wet and couldn't wait to get home and needed some immediate relief.
Everything was cool with Ty and us going forward and nothing was out of the norm. My wife wondered if he looked at the pictures and I assured her that he probably did and when she asked why I thought that I just said to trust me, they were hot. I said I am sure they help him you know what it and when the you know what dawned on her she covered her face and giggled and felt embarrassed.
By then we had gotten into taking our own pictures now and I had quite a collection growing and it always led to great sex. I even put some of them up on a website called Adult Friend Finder just to show her off. Jill was working a lot of nights since it was the holidays and a big retail season so I talked to a lot of guys at night online who thought my wife looked incredible and they all wanted to fuck her. It turned me on to know I had such a hot wife but I never shared her face or told any of them that she would meet or was into it. But I got my rocks off showing her off. She definitely had a growing legion of fans always ready for the next set of photos and there was one guy in particular that I hit it off with pretty good and would chat with about her. He was the most normal and did talk about a few things other than fucking my wife. He was married too but his wife wasn't paying him much attention.
Ty had found a girl he started dating, Ashley, and we all went out for dinner. She was very attractive and looked about like his fiancé did and similar to Jill. We had a good time and the two of them started dating seriously after that. Jill and I got home to North Carolina a couple times over the holidays.
Work picked up heavy when January rolled around and college basketball was in full swing which was our favorite time of year. We didn't see Ty as much because of the new girlfriend but he'd join us to watch games here and there. The first North Carolina-Duke game was around the corner and my wife said she wanted that night at the Park Hotel so she hoped that would be Ty's offer again. Ty showed up about an hour before the big game was to start and it was obvious he was kind of bummed. My wife asked what was wrong and he said he and Ashley had broken up.
We were bummed for him and Jill tried to comfort him. We told him he didn't have to stay for the game if he wasn't in the mood. He said no, we had a bet and he needed to be around friends. My wife asked if he would offer up the same bet for us at the Park Hotel and he agreed. We asked what he wanted in return to bet and he couldn't really come up with anything. He hummed and hawed and Jill just said to spit it out and if we didn't want to bet it we wouldn't. So he said that he had planned on taking Ashley to Durham for the second Carolina-Duke game and had already bought the plane tickets and game tickets but now they wouldn't be going.
So he sheepishly said, "I need a date for that weekend."
We looked at each other and then my wife looked at Ty and said, "So do you want us to find you a date or are you asking if I will be your date?"
He replied, "I can get a date but don't just want any date. I'd rather you be my date and just go with me as a friend."
Jill replied she wasn't sure and looked at me and we didn't know what to say. We didn't want to offend Ty as he was a good friend but weren't sure it was a good idea. It would be one thing for her to accompany him somewhere locally but his was an out of town thing.
Ty said, "I have flights leaving on a Friday morning, planned on a nice dinner that night, staying at a nice hotel and then the game is on Saturday and fly back Sunday morning. I would happily get you a separate hotel room."
Jill said we needed a few minutes to talk about it and Ty said he needed to go make a phone call. When he walked off she looked at me and said, "What do you think?"
My biggest fear was that if we said no Ty would think we weren't trusting of him. And I didn't want to upset him that way even though this was a large request. We eventually decided that Ty was a great guy and we didn't want to upset him by thinking there was a particular reason why we declined his bet offer and besides, hopefully Carolina would win anyway. When Ty returned to the table Jill informed him we had a bet and we saw his first smile of the night. Some more beer and wings came to the table and we all settled in for what would surely be another fist fight on Tobacco Road.