We enjoyed a long weekend together but soon it was Monday, back to the old grind. I knew Jennifer had a busy week, so I was surprised to get a call from her Monday afternoon at work. She told me she had a break in her schedule and had been thinking about me. We talked for a while, until she had to get back to work. She mentioned to me that she was going to call me later in the week and try to have lunch with me.
On Friday morning, Jen called and asked me if I could meet her for lunch, downtown near the Federal Courthouse Building. Since I am pretty much free to come and go as I please at my job, I agreed quickly to meet her. We arranged to meet for eleven-thirty at a restaurant that was close to her office. I arrived a bit early, around eleven o’clock, so I asked the hostess to be seated and just show Jen to my table when she arrived. I was there for about twenty minutes when I saw Jennifer walk in. She appeared to be having a conversation with several people who were trailing behind her. I was hoping, we were not going to be having lunch with all of her colleagues. It’s not that I didn’t not like them, but I felt somewhat out of place when they started talking shop. When that happened, I felt sort of uneducated for some strange reason.
I saw the hostess point Jennifer in my direction, she waved and started over. I noticed a short brunette was following her, along with three men and another blonde. So much for being alone, I thought to myself. I was relieved when the three men and one women took a table in front of me. Jennifer and the petite brunette however continued to my table. As they got near, I could not help but notice, even though small in stature, the tiny woman was a knockout. Jen is five foot, ten inches tall and maybe 135 pounds. The brunette was close to maybe five foot four, weighing maybe 115 pounds, with an incredible figure. She was wearing a tight knit dress, that clung to her petite figure like a wet tee shirt.
Jen leaned over and kissed me hello and then introduced her company.
“Jeff, I would like you to meet Tiffany, she is my personal assistant, we are together all day, everyday. I thought it was time you meet her.”, she said to me.
“Hello Tiffany, its very nice to meet you”, I said standing, extending my hand to hers.
She shook my hand and it was amazing how tiny her hand looked inside of my own. I quickly pulled the chairs out for both ladies, helping them to their seats. I saw Jennifer smile at Tiffany in a “I told you so”, look. I sat back down in my chair and motioned for the waitress to come over and get our drinks started. We ordered drinks, the ladies were given their menu’s. The ladies talked back and forth as they scanned the lunch menu. Tiffany’s voice was as tiny as her stature. She seemed almost like a doll, one that was almost too fragile to touch. As soon as the ladies decided on their selections, I called the waitress back over and we ordered. The waitress picked up our menu’s and excused herself. Tiffany spoke first.
“So Jeff, its nice to finally meet you. I have heard so much about you.”, she said.
“I hope its all good.”, I replied quickly.
“Oh yes, in fact its all very good, Jennifer gives you high marks.”, she replied, looking at Jennifer and smiling.
“Well, I am glad I get a passing grade.”, I responded.
Both of them laughed, looking at each other. I was beginning to wonder, just how much these two shared about their private lives with each other. I noticed they appeared to be really comfortable with each other, almost like one was an extension of the other. Jennifer went on to tell me that Tiffany had been working for her almost four years now and that she was invaluable. She added that without Tiffany she would be lost, never be able to get through her hectic schedule. Tiffany chimed in that it was easy with Jen, she was the best boss she ever had. I am guessing that Tiffany was maybe thirty at best, maybe even younger.
“So Jen, how is the weekend looking, you think you may be free ?”, I asked.
“I think so, we have been really busy this week, but I think it will wind down by this evening.”, she replied, looking at Tiffany.
“Good.”, I responded, looking at Tiffany, “You make sure she is free, Tiffany.”.
“I will”, the tiny woman answered, “And call me Tiff, all my friends do.”
About that time, our waitress brought our plates to us. Both ladies had ordered a small Filet Mignon that was covered in Crab Meat, topped with an Oyster sauce, a baked potato and salad. I had ordered the seafood platter that was loaded with fried shrimp, oysters, crawfish and catfish, served with spicy cajun fries. We continued our conversation as we began to eat. The food was excellent, so was the company. The topics ranged from work, to family and back again. I am not sure where it took a turn, but before I knew it, the topic had changed to a more intimate nature. Jen mentioned something about she was really looking forward to the weekend. Tiffany smiled at her and said something close to “I bet you are”, and they both laughed looking at me.
“What did I do ?”, I asked innocently.
“It’s not what you did Jeff, but I think how you did it, is the point.”, Tiff replied with a grin.
“Ok, now I am lost.”, I responded, trying to figure a way out of this conversation. Jen leaned over and grabbed my hand and squeezed it gently.
“Your far from lost, honey.”, she shot back at me, smiling.
I was trying to figure out just how much Jen may have told Tiffany, but the more the talked, the worst it appeared to get. By now, I was sure that several details of our relationship had been discussed at length, as both ladies were having a great time watching me squirm.
I was a really private person, this was very new to me.
“So Jeff, I heard you know the owner of the new club on Bourbon Street personally.”, Tiffany stated in a matter of fact tone.
“Uh, yes, we went to school together and played ball on the same team in college.”, I replied looking at Jennifer. Jennifer would not look up from her plate, pretending to be surveying what food was left.
“Well maybe the next time you two go, you could take me along. I have been wanting to go there since it opened.”, she said.
I mumbled something about, it was pretty much probably a one time thing, but if we did go again, Jennifer could let her know. I could tell by Tiff’s facial features that she knew a lot more then she was letting on. In fact, I became to get somewhat annoyed with Jennifer sharing this much of our private life with someone else. I am guessing Jennifer noticed it too, quickly changing the subject to how close it was getting to one o’clock. We all finished up and I motioned to our waitress for the check. Both ladies were relatively quiet as I waited for my credit card to come back. Finally the waitress returned, I signed the receipt and we started out for the door. Once outside, Jennifer leaned up and kissed me goodbye, mouthing the words “I’m Sorry”, silently out of view of Tiffany’s staring gaze. Tiffany walked over and put her arms out. I leaned over and gave her a kiss on the cheek and a hug. This was the first time, I was this close to her, she smelled incredible. I made a mental note to get Jen to find out what perfume she wore, it was intoxicating. Once again, I could not help but notice how small this woman was, due to how far I had to bend down to hug her. The ladies waved and starting walking in the direction of the Federal Complex, I turned and headed to the garage to get my car. I had no sooner walked back into my office when the phone rang and it was Jennifer.
“Hey, I just wanted to call you and make sure everything is ok.”, she said.
“Yes, I’m ok Jen. I was just caught off guard somewhat.”, I laughed.
“I’m sorry, I guess I talk too much sometimes. It’s a woman thing, but I swear she is my best friend and the only one I talk to.”, she confided.
“It’s ok Jen, don’t worry about it. I’m a big boy, I can handle it.”, I replied.
“Good, so I will see you tonight ok ?”, she shot back.
“Great, do you want me to get dinner on my way home ?”, I asked.
“That would be nice, how about Chinese ?”, she asked.
“Sounds good, I will see you this evening.”, I replied.
Later that evening, I left work and stopped at the restaurant, placed my order and waited. About twenty minutes later, it was ready and I headed home. It was about six in the evening, when I arrived home.
I headed in, placed the food in the oven to help keep it warm and took a shower. I was just out of the shower, when the doorbell rang.
The door opened and I heard Jen shout “Hello” and close the door behind her. She walked in, gave me a hug and a very nice kiss. She had stopped home and changed already. She was wearing white sweat pants, a pink tee shirt and running shoes. She had pulled her hair back into a pony tail making her look much younger. She bounced over to the oven and lowered the door, sticking her head inside. She reached in and took out the bags telling me she would get everything ready, for me to sit down. I headed for the great room to relax while Jen got dinner ready. I had no sooner sat down, when the doorbell rang again.
I got up and headed to the front door, not sure of who was there, I was not expecting any company. I stopped in my tracks when I saw Beth through the center glass of the door. This was definitely not good, I had to think quick. Two cars were in the driveway, so she knew I was home. I had no choice but to answer the door. I opened it slowly.
“Hi Jeff, what’s up ?”, she asked in a cheerful voice.
“Not too much Beth, just fixing to eat.”, I replied.
“Oh good.”, she fired back, “I am in time.”
“Well yes, you are.”, I said softly, “But I’m not alone.”
“I don’t mind.”, she said stepping up and into the foyer.
As I followed Beth into the great room, my worst nightmare was becoming reality. Beth and Jennifer would be in the same room. I now so much regretted not telling Jen the truth about Beth and I. Although I had no contact with Beth after I had met Jennifer, I still felt guilty.
Jennifer was still in the kitchen preparing food, when we entered the great room. I offered Beth a seat and went into the kitchen to prepare Jen.
“My sister-in-law is here, we better fix and extra plate, Jen.”, I told her.
“Oh ok then, just give me a few seconds.”, she replied.
I walked back into the great room as Jen finished up in the kitchen. I grabbed another tray from the locker and placed it by Beth. She had come straight from work, I could tell by her clothing. A red silk blouse, short black skirt, high heels and stockings. I sat back down in my chair, just as Jen entered with the food.
“Hi Jennifer. How are you ?”, Beth asked.
“I’m great, Beth and you ?”, Jen responded.
“I’m ok, thanks.”, Beth answered.
I could see Beth eyeing up Jennifer, taking in I am guessing, what she felt was her competition, although I had never made it seem that way. Beth and Jennifer struck up a conversation about family, which I stayed out of. I let the two of them catch up, but I also was ready to intervene in the conversation, in case it took a bad turn. Every time Jen would look down to get a bite of food, I noticed Beth would glance my way. I tried not to look in her direction as much as possible, feeling extremely awkward. Finally the family conversation ended, which was what I feared.
“So Jen, how are you and Jeff getting along ?”, Beth asked coyly.
“Pretty good Beth, but we are taking it really slow.”, she replied.
Beth smiled at the response, I am not sure why. Maybe it’s because it was the exact same answer I had given her days before. Maybe it was the uncertainty in Jen’s voice as she said it. Whatever the reason, it appeared to go over well with Beth.
“I guess you know, I have been having problems with Lance.”, Beth told Jen.
“No, I had no idea, Beth. I am so sorry.”, Jen responded with care in her voice.
“Jeff didn’t tell you ?”, Beth asked in amazement.
“No, we really haven’t talked much about family.”, she replied.
Beth looked down into her plate with a disturbed look on her face. I was beginning to worry that this conversation was going to be bad news. I needed a distraction, anything.
Beth went on to tell Jennifer about the events that led up to the separation and the recent getting back together of her and Lance. She basically repeated most of what she had confided to me over the past year. Jen listened intently, although I could not tell if she really was interested or just being polite. Beth went on to ask Jen, what the two of us had been doing lately. I was really relieved when Jen told her that mostly we just hung out on the weekends, not going out much. They went back and forth for a while, when I noticed Beth look at her watch.
“Well, I have to go.”, she said standing up, “It’s getting late.”
I was relieved as hell and started walking her to the door. I opened the door, she stepped out, I followed her on the porch and closed the door behind me. She turned to face me.
“I really wanted to talk to you alone.”, she told me. “Maybe later.”
With that she turned, walked to her car and got in. I breathed a sigh of relief as I opened the door and stepped back in. I re-joined Jen in the great room and sat back down to eat. A few moments passed and finally Jen spoke up.
“Jeff, I hope you know, she cares about you ?”, she asked me.
“What ?…… Well, we are family.”, I stuttered.
“No, not like family, she was looking at you like I do.”, Jen continued, “It’s not hard for another woman to see it.”
I just shook my head trying to get out of this conversation as quickly as possible. I did make a silent resolution that the first time the moment seemed right, I was going to confess to Jen, lay it all out there. I had to.
We spent the entire weekend together enjoying each other’s company, sleeping late and making love several times a day. The more time I spent with Jen, the more comfortable I was becoming with her. I decided that next weekend, I would take her someplace really nice and when the moment was right, confess to her about Beth. As I entered the new work week, all that was on my mind, was how I was going to tell her about it. What word’s should I use ?
The week passed quickly and soon I was looking at the clock, late Friday afternoon. I called Jen’s office and Tiffany answered, telling me Jen had just finished up in court and was heading back to the office. She told me she would have her call me as soon as she got in. I thanked her and hung up. Maybe fifteen minutes later, Jen called.
“Hey sweetie, how are you ?”, she asked.
“I’m fine, just waiting on you as usual.”, I laughed.
“I’m sorry Jeff, I have to work tonight, I have to prepare a motion for Monday morning at nine in the morning.”, she replied.
“It’s ok, I understand. Maybe tomorrow ?”, I asked.
“Definitely, I will call you when I get up.”, she responded.
I was getting used to having Jen sleep in my bed over the weekends. It felt cold and lonely without her and I fell asleep early just wanting the night to be over. I woke up to the sound of rain beating on the roof, it was a real down pour, New Orleans style. I got up, walked to the front and looked out. Apparently it had been raining a while, everything was drenched. I looked at the clock and it was seven - thirty. I made a pot of coffee and sat down in front of the TV. About an hour later the phone rang, it was Jen.
“Hey Jeff, I am so sorry, we couldn’t finish last night, we are back in the office again today, we will be most of the day.”, she informed me.
“Oh well, it’s a bad day to do anything, anyway.”, I replied with disappointment, “What time do you think you will be done ?”.
“I’m guessing maybe four or five this evening.”, she replied, “How about you come pick me up for dinner about five ?”
“Sure, sounds great.”, I shot back, happy that we would be together later.
I passed the day running errands, grocery shopping, washing and drying laundry among other things. I took a long hot shower, dressed in jeans and a tee shirt, left to go pickup Jen from downtown. I called Jen when I was close so she could come down and meet me. It was always a hassle to park in the city no matter what time it was. As I pulled in front of her building, she was waiting on the bench sitting there talking to Tiffany. I pulled up, reached over and opened the door.
“Hey, we have a guest for dinner, if that’s ok with you. Neither of us have our car’s, we rode in with someone else today to avoid the parking.” she stated.
“Sure, no problem.”, I responded, “Hop in.”
Jen pulled the seat back and Tiffany climbed in the back seat. She was wearing a tight pair of jeans, a pull over top and sneakers. Jen was dressed basically the same, with jeans and a tee shirt. Both of them looked incredible and I saw a few envious stares from men passing by, as they both entered my car. We pulled away and I asked the ladies where did they want to eat at. Jen replied that they had discussed it and they wanted to go to a seafood and hamburger restaurant that was close to my house. It’s well known and very good, we eat there regularly. I listened to the two of them talk about all the work they had put in on this motion and how they hoped it would be successful. Soon we were pulling into the parking lot and getting out of the vehicle. We entered the restaurant and surprisingly it was not crowded, which is rare for a Saturday night. The waitress seated us and took our order’s. Jen ordered wine, as did Tiffany, stating that they had a rough day and wanted to unwind.
As usual the food was very good, and the ladies were having a good time. They each had several more glasses of wine as they ate and chatted. The topic kept coming back to how hard they had worked both today and the night before. They both agreed they were not going to do a thing on Sunday but lounge around. That sounded good to me, a whole day alone with Jen. The girl’s ordered one last glass of wine, as we finished up.
We walked out of the restaurant and toward my car, when I had the realization I had no clue where Tiffany lived at. I could have to drive back across the river, then back, something I did not want to do. I decided I had better ask.
“Tiffany, where do you live honey ?”, I asked.
“Not far from Jen’s.”, she replied.
We pulled out of the parking lot and Tiffany gave me directions to her place. I knew exactly where it was, Susan and I had rented a condo in that area when we were first married, though I hadn’t thought of it in years. I turned into the entrance to the buildings and noticed a lot of people out in the court yards and a few utility trucks as well. I pulled up to Tiffany’s building and parked. I walked around, opened the door and let her out. About that time, a young woman, who I found out was her neighbor approached her and told her a gas line had broke in the area, the building had no gas service. That meant no one had any hot water, nor could they cook or dry clothes. She added that it would probably be late Sunday evening before the line would be repaired. As the two women were talking, Jen got out of the car and walked over to Tiffany. She told Tiffany that she could spend the night at her place and stay until the gas line was repaired. Tiffany thought a while and finally agreed, going up to her place to pack a few things for the overnight stay. We got back in the car and waited for Tiffany to return.
“Jeff, I’m sorry about this, it kind of messes things up.”, Jen told me.
“It’s ok Jen, I don’t mind, it would have been miserable for her with no hot water and no way to cook, you did the right thing. I will drop you two off at your place.”, I replied.
About ten minutes later, Tiffany returned and climbed in the car. I pulled out of the lot and turned in the direction of Jen’s Condo.
“You know I never thought to ask but did you guys have any plans ?”, Tiffany asked, “I don’t want to intrude on you.”
“Not really Tiff, we were just going back to Jeff’s for the rest of the weekend.”, Jen replied.
“Well, you drop me off at your place Jen, you go be with Jeff, I will be fine.”, Tiffany answered.
“I can’t do that, you’re my guest Tiff.”
They went back and forth for a while, I was beginning to sense that Tiffany felt bad about breaking up what was left of our weekend.
“Look how about, no one gets left alone, Tiffany you come to my house with us. I have three bedrooms, you can use one.”, I stated.
“Oh Jeff, I can’t impose on you like that, I can go to Jen’s.”, she responded.
“First, your not imposing, I invited you. Second, I would much prefer you do come, because that way, I will be with Jen, instead of alone.”, I answered.
“Yea Tiff, we can have a slumber party.”, Jen laughed.
“Good, then it’s settled.”, I said, slowing down to take a U-Turn on the highway.
It took about twenty minutes to get back to my house. I let the ladies out, got Tiffany’s bag for her and opened the front door. We all walked in and moved to the great room. I suggested Jen give Tiffany a tour of the house, show her where everything was in case she needed something. They went off down the hall to the bedroom area of the home. I took off my shoes, placed them in the locker, went to the kitchen and poured a glass of ice tea. I could hear the ladies in the back laughing and giggling, the wine was definitely affecting them.
I sat down in my chair to relax as the ladies returned.
“Jeff, your home is beautiful. I am really impressed.”, Tiffany said.
“Thank you Tiff, I really like it. I can’t imagine living anywhere else.”, I answered.
We sat and talked for a while then Jen checked the cable TV guide to see what was on. She noticed that there was a movie coming on at nine o’clock that she had been waiting to see for quite some time. Tiffany remarked that she would like to watch it as well. Looking at the time, Jen suggested we all shower, get comfortable before the movie came on since it didn’t end until after eleven. We all agreed and I went to the master bedroom, jumped in the shower, while the ladies used the other bathroom. I got out of the shower, put on a tee shirt and some loose shorts, cleaned up the bath area and headed back to the great room. Tiffany was already out of the shower sitting on the sofa watching TV. She had a long cotton shirt on that was almost knee length and had pulled her hair back into a pony tail. She looked like a teenager sitting there, hell she could almost be my daughter. I sat down in my chair and a few short minutes later Jen joined us. Jen was wearing a tee shirt and a pair of pink cotton shorts, she had also pulled her hair back in a pony tail. She plopped down on the sofa, curled her legs under her like a school girl.
“This is going to be fun.”, Jen laughed.
We all talked for a while and probably about ten minutes before the movie was about to begin, Jen suggested I make popcorn for everyone. I got up and went to the kitchen, pulled two bags from the pantry and began to prepare them. Jen came into the kitchen and walked over to the wine cooler. Susan had a built in wine cooler put in the kitchen between two cabinets under the countertop years ago, so it blended in. It held twenty-four bottles of wine, which I kept about half full most of the time. The rest of the wine was downstairs in the cellar Susan had designed. Jen bent down and open the door to the cooler.
“Is anything open ?”, she asked peering inside.
“Yes, I think the bottle of Merlot at the top is open. It’s the one you opened last weekend.”, I answered.
“Oh yea, good, I liked that bottle.”, she replied reaching for it.
She grabbed two wine glasses out of the upper cabinet and returned to the great room. I had been tempted to say something about more wine, especially considering how giddy the two ladies were, but decided against it. Every once and a while I had to stop and think about the age difference between Jen and I. I know sometimes I must have come on more like her father then her boyfriend. So I finished two large bowls of popcorn, poured my self a large glass of iced tea and returned to the ladies. I placed both bowls on the coffee table in front of us and sat down on Jen’s left with Tiffany being on her right. The movie started a few minutes later and everyone got quiet. During the next two hours as we watched the movie, the ladies finished off the bottle of wine and had opened another. I’m not going to say they were drunk, but they were feeling no pain to say the least. The movie ended about eleven fifteen, both ladies seem to have enjoyed it. Jen scanned the cable guide and found another show and quickly changed the channel.
“Jeff, I’m sort of cold. Do you have any blankets or throws I could cover with ?”, Jen asked.
“Yes in the closet in the master bedroom, there are blankets and throws on the top shelf, let me get one for you.”, I replied.
“No, I will get it. Tiff, you want one too ? “, she asked.
“Yes, I am kind of cold too, thanks.”, Tiff replied.
Jen left the room to get the blankets, I returned to watching TV with Tiffany. I noticed that Jen had been gone for quite some time. Just as I was thinking, perhaps she couldn’t find the blankets, she returned to the room with her arms full. She gave one to Tiffany, dropped the other and then turned to me.
“Um, Jeff, what is this ?”, she asked.
I looked over and was immediately jolted into severe embarrassment. She was holding a game that had been buried in the top of my closet for years. It was a sort of truth or dare board game that Susan had been given the night of her bachelorette party many years ago. It was still shrink wrapped, we had never opened it. I had no idea, it was even still there, I thought it had been thrown out years ago, why Susan kept it I had no idea.
“Where did you find that at ?”, I asked Jen.
“It was buried under the stack of blankets.”, she replied.
I went on to tell her about how it was a gift that Susan had received but I had not seen it in many years. I thought it had been thrown out.
“I see you never played it. It’s still sealed.”, Jen remarked.
“No, we thought it was kind of silly. That’s why it’s still sealed.”, I replied.
“I think we should play. How about Tiff, you up for it.”, she asked her friend with a wicked grin.
“You know me girl, I am up for about anything.”, laughed Tiff.
“And you ?”, Jen asked, looking dead at me.
“I think I’ll pass. You two can play though.”, I responded.
“No, you can’t pass, we all play.”, Jen replied, hopping back on the sofa with the game in her lap.
The ladies looked like two kids at Christmas unwrapping toys as they pulled the shrink wrap off the board game. I figured the game had to be twenty plus years old, so considering the year it was created and the climate of the times, it was probably pretty mild. I got up, headed out to the kitchen to get a refill of iced tea. I could hear the ladies giggling as they opened the box and took out the contents. I arrived back to see the board laid out on the coffee table, two different colored stacks of cards, one red, one green and several cardboard characters of naked men or women that attached to plastic stands, that you moved around the board. They quickly read the instructions and informed me on how to play. Apparently, you rolled the dice and moved that many squares on the board. If you landed on a red square, you had to draw a red card, vice versa with the green square and green cards. On the red cards there were questions you had to answer. If the other player’s thought you answered correctly, you got to stay where you were at. If you they thought you lied or dodged the question, you had to go back to the spot you were on. Same with the green cards except on green you had to perform an action. The other player’s rated the action and you either advanced or moved back to your previous spot. Apparently you just kept going around the board, there was no clear winner. You just kept playing till you began bored or aroused enough to adjourn to more pleasurable activities. I once again tried my best to get out of playing, even using the excuse I would be the judge or moderator but Jen wasn’t buying none of it.
The ladies discussed the rules for a few more seconds, then decided it was time to get started. I could tell the wine had made both of them more courageous than normal. So after a quick decision, Jen was to go first, Tiff was to be second and I was going to be last. Jen rolled first, a three, and moved into an open spot. Tiffany rolled a five and had an open spot as well. Great, I was going to be the first one carded, I had no luck at all. I was relieved to roll a three and take my place next to Jen. Jen rolled again and once again managed to find an empty spot to land in. Tiffany picked up the dice nervously and rolled a six, which landed her into a red square, which by the way was instantly the color her face was turning. Tiff slowly pulled the first red card off the top of the statement pile. Her eyes nervously scanned the words.
“Oh crap.”, she exclaimed, “Can I pick another one ?”
“No way girlfriend.”, Jen squealed, “You read the rules. You have to answer. What’s the question ?”
“ Um, it says, Have you at any time ever masterbated anyplace other than home ?”, she read softly, barely looking up from the card.
Jen bust out laughing and squealed in delight. Tiff reached over and slapped her softly on the shoulder with a look of disgust on her face. Jen leaned in intently toward Tiff like she was waiting for the winning numbers to the lottery. Tiff squirmed in her seat, looking at the card, then back at us, finally putting it down.
“Ok, I can’t lie about this one because Jen knows better. I have from time to time, uh…you know, did it at work.”, she confessed.
Jen howled in delight and was laughing hysterically, much to Tiff’s dismay. Tiff protested saying Jen already knew about it, and it was no big deal, since apparently Jen had confessed doing the same thing to Tiff.
“Just what the hell goes on in your office ?”, I asked Jen.
Both Jen and Tiff bust out laughing at the same time, I think Jen was actually crying she was laughing so hard.
“Don’t tell me you never did it at work Jeff, I know guys, you are horny all the time.”, Tiff shot back at me, “Anyway, it’s your turn, cause I answered truthfully.”
I picked up the dice and rolled a seven, once again landing me in a safe place. Jen then rolled, moving her piece the allotted spaces and she, like Tiff, landed on a red square. Tiff was elated, clapping her hands and laughing. Jen picked a red card off of the pile and began reading.
“Tell the other player’s one sexual fantasy that you hope comes true.”,
“That’s easy, it did come true, Jeff made it happen when I was with Raine. I wanted to have sex with another woman. I did it.”, she smiled.
Tiffany looked at me and back at Jennifer, she looked deep in thought. Finally she spoke up.
“Nope, that doesn’t count. It’s no longer a fantasy since you actually experienced it in real life. You have to come up with another one.”, Tiffany exclaimed.
Jen looked at me for some sort of help, but I put my hands up. I told her she was the one who wanted to play this game, accept what comes with it. Jen just sat there thinking for a while looking very unsure of what to say. Finally she blurted out an answer.
“I have always thought about having sex with two men at once.”, she answered.
“Oh really Jen, any two guys I know ?”, Tiff replied laughing out loud.
Jen reached out and slapped Tiff on the arm and told her to be quiet. I could see how this game could get really out of hand quickly. And so far no one had landed on a green or “action” card yet. I reached down on the floor and picked up the box cover and turned it over. I quickly read the introduction and judging by it, felt I was dead wrong about it.
I began to get worried.
Tiff took her turn, landed on another red card, drew a question about what was the worst sexual encounter she had experienced. She went on to mention a date she had been on, and how it led to sex in the back seat of a car. Nothing really memorable, I guess you had to be there. I rolled again and I drew a red card as well. Both ladies were overjoyed, but I got lucky and the question was to discuss how many sexual partners you had in your lifetime. Mine was easy, Susan was my first, my high school sweetheart, and then Jen. I told the story quickly, but dishonestly as I held back my relationship with Beth. The ladies looked at me in disappointment, they were hoping for much more, I could tell. I apologized telling them, that’s all there was, all the while lying through my teeth. Jen picked up the dice and rolled a ten moving her piece slowly and there it was, the first green space. Tiffany laughed hysterically and pointed to the green pile. She was urging Jen to pick one, be the guinea pig so to speak. Jen carefully and slowly, drew a green card, turned it over and read it. She quickly put it behind her back, holding it with two hands.
“No, no, no, the game is over. I quit”, she said with a serious look on her face.
“You can’t quit Jen, suck it up big girl.”, laughed Tiff, “Lemme see the card, give it.”
Jen protested but Tiff kept it up stating that we all agreed to the game and to the rules. Jen had to read the card and do exactly what it said. Jen nervously took the card from behind her back and read it aloud. It stated that she had to kiss both the player on her left and the player on her right, on the lips, for a duration of two minutes each. I, for the first time, burst into laughter, looking at Jen’s face. I could see the predicament she was in now. Tiffany had gone dead silent was just staring at Jennifer, every once in a while glancing at me. I have to admit, the sudden thought of Jen and Tiff kissing for two minutes was very arousing. Jen shrugged her shoulders, told Tiff to time her and leaned over to me. She pressed her lips to mine, softly at first, then somewhat harder. I soon felt her tongue on my lips and soon our tongues entwined in a sensual kiss. It’s surprising at how long two minutes is when you’re being timed. Finally we heard Tiff state that two minutes were up. Jen pulled away from me and I could see the anticipation in her eyes. She turned slowly and faced Tiff, I could tell she was nervous as hell. I agreed to keep time, glancing at the clock on the cable box. Jen, leaned in and placed her lips softly on Tiff’s, and began to kiss her. For the first half minute, it was pretty much bland, not much movement. But then you could tell there was a change. I’m not sure which one of the two started it, but now their lips were firmly pressed together and I sensed that this kiss had escalated. Moments later I saw Tiff’s mouth open slightly and I knew what was going on. As they both slightly turned their heads, I could see their tongues dancing together. I glanced back at the clock and the two minutes had elapsed.
“Ok, times up.”, I said.
The ladies broke the kiss, but I could tell it was an intense moment for them. They nervously looked away from each other, as Tiffany grabbed the dice to roll her turn. I noticed that Jen would not look in my direction, which kind of surprised me. After all I had saw her kiss Raine several times before, it was no big deal to me. Tiffany rolled the dice, picked up her piece and moved five spaces, she also landed smack dab on a green square. She looked at both of us in dismay but had no other choice then to pull the card. She reached down, took the card and read it’s contents. She closed her eye’s and hung her head. Jen reached over and took the card from her finger’s and read it. I saw a nervous smile cross her lips.
“Give one person in the room a very sensual, erotic massage and you must touch every body part they have, the massage must continue for a full ten minute time period.”, Jen read.
Now this was going to be good. No way she picks me in front of Jen, so I will get to see her rub down Jen right in front of me. I looked over at Tiff, who was coming to grips with her task. She looked at Jen, then she looked at me. Back and forth she went, until she spoke up.
“Jen, please don’t be mad but, can I pick Jeff ?”, she asked.
“Sure you can, that’s the rules, in fact I prefer you do.”, Jen replied laughing.
Tiff looked over at me and gave me a “what the heck” shrug and moved over closer to me. Jen suggested I lay out on the sofa and she moved over to my chair. I did as I was told and laid face down on the sofa. Jen agreed to time the event and she told Tiff to proceed. No sooner had she finished those words when I felt her tiny hands on my shoulders. She softly began to massage my shoulders surprising me with just how strong her tiny hands were. She rubbed up and down my back really pressing firmly into my flesh. It felt very, very good. Her hands moved down my back, to my waist line and hips. She firmly pushed the muscles back and forth in her small hands. I felt her hands leave me for a second, then they were reapplied to the backs of my thighs. As she kneaded my upper legs, I could not help the feeling I was getting, I knew my cock was hardening, but I was trying like hell to fight it. She moved down my legs to my calves and feet, making sure she covered my entire body. Jen suggested that it was time to roll over so Tiff could do my front. There was no way I could do that in the state I was in.
“That’s ok Jen, the back will be just fine.”, I replied.
“You wish mister, roll over and let her do the other side.”, she demanded.
I looked at Jen and saw she was determined, so I had no choice but to roll over. I now regretted wearing loose shorts, as my cock was now pushing up against them.
“Whoa, someone likes the massage Tiff. Look what you did.”, Jen laughed pointing to my shorts.
I have to say this was probably one of the most embarrassing moments of my life. I was now laying face up, my cock pushing against my shorts, in front of my girlfriend and her best friend.
“Ok, continue Tiff, you still have six minutes.”, Jen laughed.
Soon, I felt Tiff’s small hands on my legs again. She was slowly working my feet and calves up and down. As embarrassed as I was, this small woman was turning me on. When she moved up to my thighs, I thought my cock was going to tear through my shorts. I had my eyes closed, trying to think of anything I could that would get my mind off of Tiff’s touch.
“Um Tiff, you missed a spot.”, Jen squealed.
“Shut up, Jen.”, Tiff shot back.
I could feel Tiff’s hands on the upper most part of my thigh’s and it was amazing. Even though my girlfriend was only a few feet apart, I wanted more. Suddenly I felt a hand on top of my cock, squeezing it firmly. From the touch, I knew it wasn’t Jen. I opened my eyes to see Tiff, softly but firmly squeezing my rock hard cock with her small hands. It felt absolutely wonderful and she knew it. She brought her other hand up and soon, both of her hands were stroking my cock.
“Um, ladies, I think the ten minutes might be up.”, I stated, thinking of anything I could to get out of this situation.
“No ten minutes is not up buddy, so shut up.” Jen replied.
Tiffany continued to slowly stroke my cock up and down sending waves of pleasure through my entire body. There was no use in trying to fight the feeling, it was just too damn good. Suddenly I felt, a hand slide up the leg of my shorts, then with a quick motion, pull my cock out of the leg opening. I opened my eyes to see Jen sitting next to Tiff now, holding my cock in her hand. Her demeanor had become dead serious as she began to softly stroke me up and down. I looked over at Tiff, her eyes were glued to Jen’s hand.
“If you’re going to jerk him off Tiff, do it right.”, Jen whispered hoarsely.
I looked down to see Tiff’s small hand grasp my cock, her other cup my balls. My cock looked so much bigger in her tiny hands, that were now expertly pumping my shaft up and down in a perfect combination of speed and pressure. Jen moved up to me and lowered her lips close to mine.
“Does that feel good, baby, you like Tiff jerking you off ?”, she whispered.
“It feels incredible.”, I responded.
Jen leaned in further and pressed her lips to mine, pushing her tongue between my lips. With the feel of Jen’s mouth on me and the knowledge that Tiff’s small hands were jerking my cock, I was afraid I would explode way too quickly. I had to get my mind off of my cock and quickly. I pulled away from Jen’s mouth for a second and whispered to her.
“Take off your shorts baby, let us see your pussy.”, I whispered.
With absolutely no hesitation, Jen stood up and pushed her shorts down to the floor. With another motion she pushed her panties down on top of them. I reached up from where I was laying and placed two fingers into her very wet, warm slit. I heard a small almost inaudible moan as my finger touched her clit. Jen placed both of her hands on top of mine and pressed it deeper into her pussy. I looked over at Tiff, who was still stroking my cock, but whose eyes were fixed on Jen’s pussy. I put my hand out and motioned for Tiff, to move back on the sofa. When she did, I sat up facing Jen, who was standing directly in front of me. I continued to work my finger’s in her now sopping wet pussy. I glanced towards Tiffany and in all of the movement, saw that her long night dress had moved well up her thigh’s giving me a clear view of her yellow panties. I motioned for her to come closer, which she did without hesitation. I reached up between her legs and began to stroke her pussy through the sheer fabric of her panties. She tilted her head back slightly and closed her eyes. I looked back at Jen and noticed that she was focused on my hand between Tiff’s legs.
“Why don’t you take these off Tiff, they are in the way.”, I said grabbing the crotch of her now soaked panties.
Almost as if she were under a hypnotic trance, Tiff stood and pulled her night shirt up and off of her tiny body. Her breasts were small but full with large nipples, they were perfect for her size. She slowly bent over and pushed her panties to floor exposing her small but beautiful, almost bald pussy. She climbed back on the sofa next to me and spread her legs offering me access. I reached up and with my index finger, slowly moved up and down her very wet lips. Jen stepped back off of my other hand and knelt down on the floor next to me. She reached down and began to stroke my cock as she watched my fingers play with Tiffany’s pussy. Tiff reached one hand down and gently caressed my balls, as Jen stroked my cock. I had my finger now rubbing Tiff’s clit in small quick circles, which was beginning to have quite an effect on her. I reached up placing one hand on the back of Tiff’s neck, pulling her face down to mine. My lips met her small mouth, my arms wrapping around her tiny body. She immediately opened her mouth inviting my tongue to join hers, which I immediately accepted. She hungrily kissed me back flicking her tongue in and out of my mouth. I suddenly felt another pair of soft lips on my face, it was Jen. I broke my kiss with Tiff, turned and pressed my lips to Jen’s. I have said before what an incredible kisser Jen was and soon I was lost in another mind numbing kiss with her. I felt Tiff slide down my body allowing Jen full access to me. As I was enjoying Jen’s tongue in my mouth, Tiff’s hand once again wrapped around my cock. It was immediately followed by her mouth, as she sucked the head of my cock into her small, wet mouth. I have never experienced such an incredible feeling in my life. One woman kissing me passionately on the lips, yet another taking my cock into her mouth. Jen must have sensed my pleasure because she interrupted our kiss briefly and looked down at what her friend was doing. She moved down to join Tiffany, taking hold of my cock and pumping it slowly into her friends hungry mouth. This went on for a few seconds, until Jen pulled my cock from Tiff’s mouth and placed it in her own. She began an immediate intense suction on my cock sending me ever closer to an orgasm. I had to push Jen off of my cock for fear of cumming too quickly, I wanted this to last.
I sat up, turned and faced Tiffany, I gently pushed her back until she was lying on the sofa in front of me. I lowered myself down slowly until my face was just inches from her pussy. I extended my tongue and touched it to the bottom of her hot, wet slit. I slowly licked her pussy from bottom all the way up until my tongue was softly brushing against her small clit. She tasted much different then Jen, her fluid was thicker, sweeter. In a matter of minutes I had her hips dancing on my face. Jen moved up and sucked one of Tiff’s nipples into her mouth. That was all it took. Tiff moaned loudly, grabbed my head with both hands, pressing it deep into her pussy. Her body bucked and thrashed as waves of pleasure hit her every nerve ending. She rode wave after wave of pleasure until the feelings subsided inside of her. She reached down and pushed my forehead away, separating my mouth from her pussy.
“Oh God that was good. It’s been so long since anyone has went down on me.”, Tiff panted.
I raised up and got back into a sitting position giving Tiff a chance to recover. She got up as well and pushed Jen down into the spot where she had been. Jen laid back, spreading her luscious thighs exposing her soaking wet pussy. I began to lean forward in preparation to suck Jen’s juicy pussy when Tiff grabbed my shoulder pushing me aside. I moved over as she requested, wondering what she had in mind. That question was answered quickly as Tiff quickly lowered her mouth on Jen’s pussy, sticking her tongue deep inside of her friend. Jen arched her back in response, as she exhaled deeply. The sight was absolutely incredible, my beautiful girlfriend laying back, her legs spread having her pussy licked by this gorgeous little brunette. I sat back and just watched for several minutes taking in the breath taking view. I knew from past experience Jen was hurtling quickly toward her first orgasm. I got up and moved behind Tiffany reaching down and lifting her up off the sofa by her hips. She knew exactly what I had in mind as she raised her ass in the air, opening her legs allowing me to get close behind her. She raised her mouth off of Jen for a second and turned towards me.
“Jeff, go slow, its been a while since I have been fucked.”, she said.
She reached up between her legs and grabbed my cock guiding it to her wet opening. I gently pressed the head of my cock between her warm, wet lips. I felt Tiff pushing back against my cock trying to help me get inside her. I pushed against her once more and the head of my cock popped into her pussy. I felt her let out a gasp, as I entered her. I froze for a few seconds, letting her get used to my cock inside her. Her pussy was very small and extremely tight, it gripped my cock like a vise. She lowered her mouth back down on Jen’s pussy and began to suck her clit with renewed interest. I slowly began to move my hips, pushing my cock in and out of her tight pussy. After a few long, very slow strokes, I was deep inside of her, my hands on her hips, pulling her onto my rock hard cock. Jen began to breathe heavily, making small whimpering sounds, I knew she was close. I began to pump Tiffany faster, slamming my cock into her tiny pussy. Jen let out a long soft moan, then erupted into an intense orgasm, crying out in pleasure. Watching Jen in the throes of orgasm, enjoying her girlfriend’s tongue, sent me over the edge. I pulled out of Tiff’s tight wet pussy, grabbed my cock with my right hand, pumping it rapidly towards her ass. The first spurt of cum shot out and landed on Tiff’s back, then wave after wave of hot cum spilled out, covering her small, tight ass in gobs of white milky cum. She reached back with one hand, grabbing my cock pulling on it, milking the last few drops of cum left in it. We all fell back on the sofa, spent, trying to catch our breath.