Trapped Ch. 01

Before last summer, Jill and Dan was a typical married couple living in the Midwest. They had married young and were both now in their early thirties. Everything seemed to be falling into place and going very well for them. Jill, with her long curly brunette hair, sparkling blue eyes, petite tennis player physique, and a joyful personality, had an innocent sex appeal that she was unaware of. Because of her conservative parents, Jill had not dated very much. In fact, Dan was the first guy that was able to take Jill on a date that was not chaperoned. Being raised this way made Jill a bit naive and ultra conservative, in and out of the bedroom.

Jill recently landed her dream job as a chemistry teacher at the same prestigious, conservative high school that she attended. As a matter of fact, many of the administrators and teachers that were there when she attended the school remained on the faculty. Jill cherished her position at the school.

Dan, on the other hand, being relatively handsome, exercised regularly and had been exposed in his early teens to some sexual experimentation, mostly in the back seat of his car, even “going all the way” a few times before meeting Jill. Recently, Dan had become a bit frustrated by Jill's inhibited sexual attitudes and conservative points of view, and he often wished she was a bit more “adventurous”. Dan works as a software engineer for a large global technology company that lately had required a lot of travel visiting customers and business partners. During the evenings alone in his hotel room Dan begun to fantasize and masturbate to relieve his sexual tension and frustration. Each week his fantasies would become more and more risque as he pictured Jill in many different scenarios. Dan knew that he could never share these desires with Jill, since she would never understand.

However, the work experience had been great for Dan's career allowing him to meet many influential and interesting people. Each project elevated him higher and higher in his management’s eyes. Dan was next assigned to assist a deal with a critical business partner for a long term engagement. Initially, Dan was apprehensive when assigned to this account, since he heard some “horror stories” about the owner, a man named Bruce. With a single screw up or error, it could be Dan’s career, his livelihood, and his family’s long term security since it would force him to start out all over again.

Fortunately, Bruce and Dan hit it off very well. Bruce, a former military officer, took the role of mentor and Dan the protégé. Bruce, a tall black man was blessed with a very athletic physique, like a muscular wide receiver and he possessed a natural charisma. Bruce was a natural leader and every move he made was carefully planned and executed. Dan could not help but to admire Bruce.

Since Dan was spending so much time at his company, Bruce decided it was time to introduce Dan to his wife, Deborah. "Hey Dan." said Bruce, as they were closing up, "Do you have any plans for dinner this evening? I know it must be getting kind of lonely being by yourself every night, how about you coming over to my house this evening for dinner?” Dan smiled and quickly agreed to his offer.

Dan received directions from Bruce and promptly arrived at the time Bruce stated. Dan knocked and was greeted by Bruce at the door of his impressive home. As he entered through the foyer Dan was noticing the spiral staircase leading to the upper levels and admired the art work and handsome furniture placed throughout. Bruce opened the dark polished wood doors to his den and offered Dan a drink. As Dan sat down Bruce called for Deborah to come out, so he could introduce her. Dan was a bit surprised to see such an attractive woman come into the room. As Dan’s eyes started to roam over Deborah he admired Deborah’s long light brown hair and a face that was “model pretty”. Deborah even had a great smile that seemed to warm the room. What clearly set Deborah apart from most women is her figure, she had some of the most beautiful long legs and perfectly formed full breasts that he had ever seen. Deborah was wearing an almost transparent blouse and it was clearly evident that she wasn't wearing a bra as her erect nipples pressed against the silky material. Dan observed that Deborah’s breast seemed to defy the laws of gravity as they lightly swayed as she walked towards him. Dan thought, “Man, this is one sexy lady, and she seems to worship the ground that Bruce walks on, my man Bruce has it made!”

After initial introductions and some small talk about how things were going at the office Deborah lead them to the dining room where she had their meal presented. The evening went extremely well as the three of them got along superbly. They discovered many areas of common interest. As they sat and talked, after retiring to the study, Dan kept glancing at Deborah and sensed a mild flirtation being exhibited. Bruce didn't seem to mind and Dan flirted back as well, thinking if he later got caught he could blame it on the wine.

Deborah and Bruce hosted Dan many more times that spring. They both seemed very curious about Jill, since Dan mentioned her so often to them. Deborah took the initiative one day to phone Jill. Deborah and Jill enjoyed a long conversation and Deborah suggested to Bruce that she would love to meet Jill in person someday soon. At dinner one evening, Deborah asked Dan how he could spend so many long hours alone in the evenings. Dan told her that he sometimes uses the internet to chat and unwind, calls home and talks with Jill and reviews the project plans for the next day. Chatting on the internet intrigued Deborah. She asked Dan what chat name he used, suggesting, with a sly smile, that perhaps, they could chat sometime soon.

Dan returned to his hotel room and called his wife to see how her day went. After hanging up Dan sat in his bed thinking about Jill and how much he wish she was in his bed now to help him with his raging erection. Dan on impulse decided to chat a bit to "wind down" a bit before going to sleep. A part of Dan was hoping to see Deborah on-line. As Dan signed on he immediately received a greeting from Deborah. Dan sent her a message and she immediately responded back again. They started an interplay that went on for several hours. Deborah told him that after all this time, she still had no idea what Jill looked like. Dan sent Deborah the URL of Jill's school’s web page, so that she could see her picture. Deborah commented, "She looks very cute, I can see why you miss her so.” Deborah added, “Bruce has always found demure looking women like Jill to be quite sexy.”

During their chat Deborah brought up again about how it must be hard for a guy to be away from home as often and for as long as he is. She told Dan, "Bruce can not go more than 3 days without sex, so I don't know how you go without for so long on a regular basis." Dan laughed and wrote back, "There are other ways to handle my urges". Deborah inquired, "Exactly what do you mean?" He sent some vague comments, but Deborah persisted. "Please describe what you mean." This banter kept on and on until finally Dan confessed to her that "I've sometimes have met ladies on the web that would cyber with me, and every once in a while give me a little peek at them with their web cams." Deborah responded, by asking more and more personal questions, like "What things turn you on?" and "What is your greatest fantasy?"

Dan does not understand why, but when he chats it seems like all of his thoughts just come out on the keyboard. He spilled the beans by telling Deborah that "I have fantasized about seeing Jill with another man." Dan apologized for offending her, but she reassured him that "Your fantasy is quite normal. So, don't worry about it your fantasy is safe with me!" He really enjoyed chatting with her in the evenings and found himself looking more and more forward to them each night.

One night as Bruce was at a late night meeting, Deborah wrote Dan a message stating, "I have a surprise for you!” Deborah then instructed Dan to accept her invitation to a private chat room she created. Dan followed Deborah’s directions and was surprised to see her icon with a web cam function near it. Dan clicked the web cam icon and was happy to see Deborah appear. Dan found seeing her to be a nice addition to their chatting and somewhat erotic, especially with the cleavage showing from her shirt. Deborah confessed, "I'm feeling a bit horny with Bruce being gone." She asked, "Would you secretly consider ‘cybering’ with me just this one time?"

Dan was not thinking with the right head and he quickly agreed to her offer. As he watched the screen, Deborah played a little strip tease just revealing a little bit of her delicate lace bra. Her cam was positioned to just show her top to Dan. She wrote, "Come on, I feel like I am playing all alone here, at least turn your cam on, so that I can see the expressions on your face!” Dan turned on his cam and invited her to view it. Dan did not notice that his camera slipped a bit from position, so that the camera was aimed right at his crotch. Dan was thinking he would stroke himself as Deborah teased him a bit, since all she could see was his face, so he removed his pants and underwear. Dan began stroking as Deborah undid her 36D bra. Dan climaxed as soon as he saw her nipples harden from the touch of her hand. He wrote and apologized for getting so carried away. Deborah laughed and wrote back, "You've made my day knowing that just the image of my breast could still affect a man." Deborah kept it a secret from Dan that his cock was in full view to her during their chat. Deborah knew that Bruce would be very happy with her progress with Dan.

Later that week, Bruce called Dan into his office. "Dan, sit down please." He then activated the intercom and asked Deborah to come into the office. Deborah sauntered in carrying a video tape. She placed it into the VCR and pressed Play. Dan's surprise and embarrassment was quite evident as he saw his entire "web performance" right there on the screen, as did Bruce and Deborah. Dan nearly died seeing his cock explode in front of them. He felt even worse as the cam captured his cock shrinking to its small faccid state. Bruce said, "Dan, I understand why you did it, but I want you to know that all I have ever seen of your wife is that one modest picture on the school's web page and that you practically had sex with my wife."

Bruce then asked, "Dan, what do you think we should do about this unfair chain of events?" Dan was dumbfounded and sat there as Bruce told him, "I am also aware of your fantasy of seeing Jill with another man, Deborah has told me everything!" Dan just turned red from embarrassment. "I am going to be candid with you, my birthday is coming up, Dan and I desire to be that man!" Dan tried to explain to Bruce, "Jill would never go along with it." Bruce responded, “You just leave that part up to me, you just do as I say and Deborah and I will work out the details. Is that understood?” Dan gulped and nodded affirmatively.

Dan did not want the tape to expose him, causing him to possibly lose his job, maybe even lose Jill. Dan agreed to Bruce's demands and Bruce said, ”I will make you a deal, if Jill does not flat out ask me to fuck her, then I will not go any further with her and promptly destroy the tape.” Bruce added, “All you need to do is not get in the way, do you understand?” Again, nodding yes, Dan resigned himself to Bruce’s terms thinking that his Jill would never agree to an affair. Truth be told, Bruce had Dan against a wall, and Dan knew it, but the last clause gave Dan a ray of hope thinking that if this all rested on Jill willingly spreading her legs for Bruce, then he was in the clear. Dan followed Deborah to the small meeting room next door so that she could learn everything she could about Jill. This interview would aid her and Bruce to create the perfect plan. If Dan did not comply, Bruce said, "Your career would be over. You give me any trouble on this or put up the least bit of resistance and your dead meat. Got it?" Bruce added, “Besides, if your wife is half as conservative as you say, I will not even get to first base, right?

The first thing that Deborah asked Dan to do was "Remove your pants and underwear." On the table was a tape measure and he feared what would come next. Being so nervous, Dan was at a flaccid state as he slowly removed his underwear. Deborah placed the tape over his cock and wrote 2 1/2" on her notepad. Deborah then slowly unbuttoned her shirt to reveal her breasts to Dan, and immediately Dan became erect and he nearly lost it as she grabbed it and stroked it to make sure it was at full erection. Deborah smiled as she saw the head barely pass the 5" mark on her ruler. Deborah asked Dan, "Are you a bit self concious about having a small cock?" This was because Dan regained his composure and tried to shield his erection from Deborah's eyes. Deborah asked, “Has your wife ever been curious on how big you really are?” Dan just ignored her question and asked "Can I put my pants back on?" Deborah told him "Okay." Then she said, ”Don't worry, the rest of my questions are only concerning your wife." She asked, "How tall is Jill and what size clothes does she usually wear?" He replied " 5'4" and a size 7". Deborah added, “Does Jill drink or smoke?” Dan replied, “Jill has never smoked and only once on our honeymoon did she try a glass of wine. I can still remember how “woozy” the one glass made her, Jill did not like how it made her feel less in control.” Deborah then asked "What's her bra size?" He told her "34A, or nearly A, depending on the style." Deborah laughed, "No wonder you got so excited by seeing my titties", as she wrote down these details. Dan added, "She is a bit self concious of her small bust." "Like you are about your small cock?", Deborah added. Dan just lowered his head and nodded, wishing he was not so weak to Deborah. Deborah asked about Jill's dating life and could not believe Jill's limited experience, but Dan confirmed that he was the first guy to date her alone since her Dad was very strict. Deborah asked Dan about their sex life and Dan admitted that it mostly consisted of the missionary position and how Jill viewed oral as perverted. And "Yes, I am her only lover." Dan was surprised when Deborah asked, "Does Jill ever shave, I mean her crotch?" and he laughed and said, "No way, she is quite bushy and has never even been tempted to shave. In fact, she only trims enough to wear her swimsuit in public." Dan added, "Jill feels that if her bush was gone that she would look like a 12 year old naked, or at least that is what she tells me when I ask for her to shave it off for me on my birthday. I do love how full her bush is, but yes, every once in a while I am curious on how she would look shaved. I have secretly wondered if she would be more open to oral sex after experiencing it with a smooth slit, but so far it has just been a dream."

For the next hour Dan told Deborah everything she wanted to know. Dan had never been through such a thorough interview. Deborah then phoned Jill and said, "Bruce and Dan have planned a long romantic weekend away to celebrate a "new contract" and thought that it would be a good time for everyone to finally meet." Jill and Dan had not had a trip for just the two of them in years. "Oh, that sounds great", Jill readily agreed to Deborah's offer. Jill admitted, "You know, I've heard so much about you and Bruce from Dan that I am really looking forward to finally getting the opportunity to meet you both face-to-face." Deborah told her "The guys will be working out of town thru Friday afternoon, but, you should plan on flying in on Thursday morning. That way, we can get to know each other better." Deborah then added, "I'll meet you at the airport gate, so that you won't have to worry about getting to the resort." They continued their conversation about what Jill should bring and her flight schedules, so that at the end of their conversation Jill was thoroughly briefed on the plans.

Thursday arrived and Deborah walked to the gate where Jill's plane landed. Since Deb had seen Jill's picture, she called out to her and gave her a hug and told her "I'm so glad that you finally decided to visit." Deborah pretended to be surprised when Jill was unable to find her luggage. Deborah told her, "My sister works for the airline and I'll have her see to it that you receive your bags as soon as possible. In actuality, this was part of the plan and had been arranged in advance. "Besides,” Deborah told her, “it gives us a good excuse to do some shopping!”

Deborah and Jill hit it off right from the start, but Jill was surprised to see a man in the car when they reached it. Deborah introduced Jill to her husband, Bruce and informed Jill that "He was able to take off early and I hope that you don't mind him tagging along with us." Jill, never one to make waves, said, “I don't have a problem with it." Deborah informed Bruce, "Jill's luggage didn't come in at baggage claims. We will have to get her some things for tonight and maybe go shopping tomorrow if they don't show up by then."

Jill spent the whole day with Deborah and Bruce and had a great time as she tried on different outfits, finally settling on a beautiful dinner dress that Bruce had suggested to her. Jill found Bruce's confidence re-assuring, finding it easy to trust and follow his lead. Finally, they arrived at the resort and each retired to their respective adjoining rooms. Later in the night, Jill lay awake in bed and started to blush when she overheard Deborah's many screams of ecstacy during the evening. Jill wished her husband was with her since she was feeling in the mood, too.

The next day, Jill was disappointed to see that her luggage had not yet arrived. However, she was more surprised to see a "gift" at her door from her husband. Jill picked up the box and was met by Deborah as she opened her door to retrieve her newspaper. Deborah asked Jill what she had in her hands, knowing full well what it was since she placed the box there earlier. Jill told Deborah, “It is a gift from Dan, he heard about me losing my luggage from Bruce.” Deborah suggested that Jill step into her room, so that she could open Dan’s gift and offered Jill a glass of her “breakfast punch”, which she thankfully accepted. Jill read the attached card out loud, “Darling, I know how much you love the water so I called the hotel gift shop and bought you a swimsuit, so that you can enjoy a morning swim.”

Jill was worried that it would be something risque, but was pleasantly surprised to see a white one piece, similar to her favorite swimsuit she had at home. Deborah told Jill, “Bruce left to go golfing with some business associates I suggest that we get a quick swim before lunch when all of the other tourists would begin to arrive. If we go out now we will have the whole pool to ourselves.” Jill liked the idea of swimming without a bunch of other people trying to check her out, so she agreed to Deborah’s offer. Jill gulped down the rest of her “punch” and asked Deborah when she would like to meet. Deborah replied, “meet you in the hall in 10 minutes”. So Jill hurried to her room so she could change into her new swimsuit.

The girls met each other in the hallway in their swimsuits. In her rush to get into the new swimsuit Jill did not realize that her new swimsuit was quite different than her tried and true one lost in her luggage. In fact it was cut very high up her legs and was quite thin and transparent. The swimsuit did not have any lining, so it was very revealing, even though it was dry. When wet, she would discover that it would become almost transparent. Jill was surprised to see Deborah arrive in the hallway in a very skimpy, revealing bikini. It was not until this moment that Jill realized how busty and well built her new friend was. Jill felt like a young school girl next to this rather shapely woman and felt even more intimidated as Deborah's eyes traveled up and down Jill's petite frame. Jill instinctly crossed her arms over her bust thinking that Deborah was comparing their figures. Deborah said, “Jill, there is no way that you can go out in public like that!” Jill just stared in unbelief at Deborah and wondered why she would make such a remark since Jill felt that Deborah was dressed in a far more skimpy and revealing swimsuit than hers.