The Big Tease

Logan had just arrived and was ogling Jan with a lecherous smile when her doorbell rang. "I'll see who it is", and he went to the door. "Hi Don, your timing is perfect. We were just going to Vic's for lunch and it's my treat."

"Then this is my lucky day."

"It certainly is." He turned around and called to Jan, "We have company joining us for lunch." Her heart skipped and she quickly looked down at her breasts.

"Damn him", she said to herself. "When will I learn that the easiest ones are always the hardest ones. Coming," she called out and went to find Don standing there. She stopped in the middle of the room as he stared at her with his mouth open. Logan was standing to one side taking it all in and smiling like he'd just won a lottery.

"Shall we go?" Jan kept looking at Don's face and he kept looking at her chest and face. As they neared the car Logan said, "Damn I forgot my keys, Don would you mind driving."

"Of course not." Logan quickly held the front door for Jan and he got into the backseat. He was going to enjoy the almost thirty minute drive as Don tried not to look and Jan tried to figure out where to look and how to sit to minimize her exposure to Don. To make matters worse she could see Don's erection pushing against his Dockers. Showing so much cleavage to strangers was bad enough but this was Don her very close friend and she was very nearly showing him more than just cleavage. From her point of view she could look down and see aureole but based on what she saw in the mirror she didn't think he could see that much.

They had a very nice lunch and Jan settled down as she got used to her awkward situation. It was a dare after all not a lifestyle and in a while it will be over. She just felt sorry for teasing Don. He was just getting caught in the crossfire of their game of dares and pranks and that wasn't right. They went back to Jan's and Don said, "Thanks for lunch Logan."

"You're welcome." Don stepped over to Jan and giving her a warm hug said in a softer voice, "Thank you for making my heart race and my eyes dance."

"You're welcome. Maybe we can get together for lunch or something next weekend."

"I'm your servant." She kissed his cheek and Don left. Once inside Jan told Logan, "That wasn't a very nice thing to do to your friend."

"Are you kidding, he was having a great time."

"It isn't that he didn't enjoy himself but don't you think that's pretty rough on him?"

"He's over his divorce, looking for a woman and getting on with life, he said so himself."

"Maybe he said that so you'll stop nagging him about finding a woman."

"I don't nag him."

Jan let it drop then but she still didn't think that lunch with Don had been such a good idea even though she liked having him look at her so much.

Logan left Monday morning for Winchester, Virginia, just west of Washington D.C. and by Monday night Jan had a dare for Logan, and she finally felt like she had a halfway challenging one too. She planned to wait until he was about halfway through his project before she would issue the challenge but she didn't. In fact it was almost nine o'clock Monday night when she called him and said, "Okay I have a dare for you."

"So soon."

"Yes. Where are you staying?"

"I had to settle for the Super Eight because they overbooked my hotel."

"What floor?"

"The third, why?"

"Patience. Okay, here is your challenge. You will get naked, wrap one towel around your waist and go get ice."

"Okay that's just down to the end of the hall."

"Now wait. I mean the ice machine on the ground floor. Take your little ice bucket and go to the first floor, fill the ice bucket and return to your room."

"The ground floor?"

"Yes and of course you must take pictures. At least one of you in your towel and one with the towel either open or removed altogether and be sure a sign proving you are on the ground floor is in both pictures. Oh and one last little detail. I have to see the pictures before I go to bed at eleven. Do you accept?"

"Damn you have come up with a tough one this time. Can I have at least until midnight?"

"Nope. I have to be asleep before midnight or I'll be too tired tomorrow." He hesitated and she thought she might have him at last, but he wasn't about to let her get the best of him. Besides he knew that he could do it so he said, "Okay I accept." She hung up the phone and smiled. She knew that the towels at the Super Eights that she had stayed in were on the small side and that made it even better than she had hoped. He would have to be very careful and hold the towel very tightly if he was going to succeed without having a crisis. Plus by her adding the complication of the ice bucket his task would be even tougher. That would ensure that he had only one hand to hold the towel corners and protect his modesty. Logan looked at his watch and planned to wait until ten forty five to take his very risky walk downstairs.

He was naked and practicing with the towel and looking at himself in the mirror by ten thirty. There just wasn't enough towel to go around him and overlap itself so there had to be a gap. The only possible option for the gap was over a hip unless he wanted his cock or ass to be exposed. Janet was getting very good at the game and it was time for him to go. With a firm grip on two corners of the towel and the ice bucket and his plastic room key and phone in the other hand he went out into the hall. So far so good, the hallway was empty. He went to the elevator and stood there for what seemed like an hour before the elevator took him to the ground floor. When the door slid open he held his breath and stepped out but again the hall was empty. He stepped quickly to the end of the hall and as he put the ice bucket on the tray his towel started to slip. He quickly grabbed the towel with both hands and averted him being exposed, but in the process he dropped his room card. He bent over and picked that up but the stress on the towel pulled that out of his hand and it fell away completely. He was getting rattled now. He grabbed the towel and got that back around him and then looked up and down the hall but he saw nobody. He still hadn't filled the ice bucket so he held the button in and waited until he had gotten his ice. He felt in control once again and headed for the elevator. Then he figured that the stairs would be safer. If as he climbed the stairs and he dropped the towel it wouldn't be a crisis because almost nobody used the stairs. He just had the door open when the room door behind him opened and a guy came out, openly stared at Logan as he passed and went on. Logan made it up the first flight of stairs but his towel had slipped free within the first ten steps so he figured screw it and kept going. Then he remembered he hadn't taken the damn photos.

With his towel dragging behind him he went back downstairs and covered himself just before reentering the hallway. He retraced his steps and took a photo of himself at the elevator showing the floor number in large letters. But he still had to take one while he was exposed. He put the ice bucket and his key on the floor, straightened the towel and looked up and down the hallway and it seemed safe so with his heart racing he whipped the towel off and took the picture. Unfortunately for him the elevator opened and a guy stepped out. "Buddy you better get your ass covered or some lady is going to call the cops." That incident had him so rattled he almost forgot his ice bucket and room card. He put himself back together then and headed for the stairs at a near run and felt the towel slowly slipping from his grasp. Once he was safely behind the stairway door he yanked the towel off and sprinted up the stairs to the third floor.

He took a minute to catch his breath, positioned his towel and exited into the hallway. He made it all of ten or fifteen feet before he stumbled, his ice bucket clattering on the hard carpeted floor, his room card falling and in his effort to catch either the ice bucket or the card he dropped his towel. The clattering ice bucket sounded extremely loud to him when it hit and understandably, once again his nerves failed him. He bent down to grab the ice bucket before getting his towel back around him and the noise brought an older woman to her door to investigate. Logan heard her door open at the same time that she saw his naked ass pointing at her. "Oh my God I can't believe this", and slammed her door. At that point he figured to hell with it and raced for his door with the towel flying behind him like a flag and the now empty and broken ice bucket and his room card in his right hand. He finally made it and slammed his door behind him. His heart was racing and he was out of breath but he was in his room and safe and he had his photos to prove that he had met his challenge. If she ever came up with a worse dare he would have to admit defeat. She had found his limit but he wasn't about to ever tell her that. Now he had to find her limit.

Chapter Seven

Logan quickly got the photos on their way and spent the next two hours thinking up the most daring challenge for her yet. It had to be something that was possible to do and not illegal or physically dangerous. He knew that she would break her neck to do about anything he could throw at her. He knew she did not want to have to say no to any challenge. But this time he would not do anything that would suddenly surprise her. She did not like to be scared like she had been with the rubber cock. Anything like just getting naked on top of a building or any of the other things he had come up with wouldn't be enough of a challenge for her. This might be the limit, the last dare for them so it had to at least be equal to him getting caught bare assed twice, flustered and even frightened. He finally had to accept the fact that he had to get even and plan accordingly.

For the next two evenings Logan thought about past stunts. She didn't mind showing herself off and in fact she seemed to like it...to a point. He just didn't know what that point was. She never complained about showing her breasts at lunch, only that it might bother Don. She never gave a hint that she minded getting naked on top of the Madison building and then also going from there back to work without panties. So his plan had to include those elements so she would be more inclined to go along with his plan. He had a plan in no time. Some of it would even be a repeat of what she had already done. She would even have a choice of two directions to go for the last part of the dare. It would be legal and safe and would not include anything frightening at all. In fact everything would be spelled out to her before it happened. Yes this was the perfect challenge, for her and for him and he could hardly wait.

He waited until Friday night and called her. "I assume you got my pictures."

"Yes I did."

"I just want you to know that was a very difficult dare."

"And I thought I was giving you a fairly easy one." He proceeded to tell her of his complications and it was all she could do not to bust out laughing. She finally got him and got him good.

She got control of herself and said, "But you succeeded and you survived."

"Yes I did. Now I have another one for you."

Oh and so soon, okay." She sounded very confident and ready but he knew she was going to sputter with this one.

"Okay here it is. We'll start out just as you were at the restaurant last week...but with a change. You'll wear your shortest skirt which is I believe that black one."

"Yes it is." "And the same top with those eight little buttons undone."

"Logan that will put me at risk of falling out again."

"Yes I know especially since you won't be wearing a bra."

"Our rule is we can't be arrested."

"You won't be arrested."

"I think I will, where will I be going in this outfit?"

"Someplace safe...to Don's."

"Logan we've talked about this before."

"It will be fine. I've sent him an email and there will be no surprises like rubber dildos or frightening moments. I won't do that to you again."

"Logan you are playing with fire."

"We play with fire every time either of us does a dare."

"This isn't the same."

"Are you saying you won't do it...that you are saying uncle?"

No. I'm just giving you fair warning."

"Consider me warned then. So will you do it?"

"I'll do it." He knew she would. He knew she just couldn't say no. To her a dare was like a red flag to a charging bull and that played right into his needs.

"Wonderful, I'll send you an email with the detailed instructions."

"Logan maybe we better talk about this when you get back."

"Okay." She was going to ask for a truce. They only talked another couple of minutes and then hung up.

The email came in a couple of hours later. It was just as he had said. Wear the black short skirt and the same soft green top with no bra. Then she tried on the top without a bra and with the eight buttons undone again and stood in front of the mirror. So much of the area between her breasts was exposed as well as most of her breasts. As she stood there at the mirror she imagined poor Don looking her and she watched as her nipples pushed out against the fabric. There was so little of her that was still covered by that pauper style top and what was covered was clearly defined by the stretching double knit fabric. She felt so exposed and indeed she was. There was no way she could ever go out in public looking as she did and Logan had to know that. So then why did he see it as okay that Don would see her like that?

As she drove toward Don's Saturday afternoon she felt restless and even nervous. She looked down at her exposed legs and her nipples were stiff and pushing back against the tight fabric and it seemed the closer she got to Don's the stiffer and longer they got. She decided it was a little like a young man getting an erection on his way to a date. The closer he got to his date the bigger his cock got. Just like her nipples were doing.

When Don saw her his eyes widened and he stared at her. He was lost for words and just stepped back to let her in. As she walked in front of him he watched her ass and her legs all the way up to where they disappeared under the skirt and not far from her ass cheeks. He took a long step and put his arm around her and asked, "Something to drink?"

Her voice came out soft as she said, "Yes, something strong."

"A taste of scotch?"

"That's a start." He smiled and released her to fix their scotch on the rocks. They tapped glasses and took a taste of the golden fire and then Don said, "I would have thought that Logan would have learned his lesson."

"Don if you don't want to be part of this..."

"Jan...I can't stop looking at you so unless you want to call it I'm staying with you."

"I told Logan this wasn't a good idea but he insisted. I could have said I give and I know that, but I guess there is a part of me that didn't want to, even if it caused you a problem."

"The only problem it causes me we won't talk about. After we had lunch last week I came home in a pretty rough state of mind."

"Don..."

"Jan it's okay. My problem isn't just because I could almost see your breasts. It's something else."

"Can we talk about it?"

"Maybe another time. Now when I look at you and see even more of you I know I'll have to have a long talk with myself later, but I can't stop looking at you and I mean all of you not just...well you know."

Before either of them could say more the phone rang and Don checked the caller I.D. "Hi Logan.

"Hi Don, is Jan there?"

"Yes, just a sec." He handed her the phone and she said, "Hi."

"Hi, having fun?"

Rather than really answer his question she said, "I'm having a scotch on the rocks."

"Have one for me too. Okay there are two more parts to this dare. Tell Don I want him to undo the rest of the exposed buttons on your blouse." "Logan you know what will happen."

"Maybe not, let's see. Tell him what you want him to do while I wait."

"Don will you undo these other buttons on my top?" Don looked at her and she looked right into his eyes and waited as she held the phone to her ear and slowly nodded her head up and down.

Chapter Eight

Don's hands went to her top and as soon as he touched her she caught her breath and told Logan, "Don's undoing my top right now."

"Are you falling out?"

"Not yet."

"But it's close."

"Very close. There goes the last button Logan. What do you want me to do if my breasts do come out?"

"That's up to you, leave them out or try to pull your top over them again...or better yet have Don do that for you."

Jan's cheeks were flushed as she asked, "What now?"

"Enjoy your scotch and each other's company and I'll call back in a little bit."

"Logan are you sure you know what you're doing?"

"Of course, I'm giving you your biggest dare yet."

"That's true. This is the biggest test in my life in fact."

"Fantastic. I'll talk to you soon," and he hung up. Don put another splash of scotch in Jan's glass and she said, "He's going to call back in a little bit."

"What did he say when you asked him about you...having an accident?"

"He said it's up to us what I do."

Don's cock looked like it was so hard that it had to hurt. She wouldn't blame him a bit if he were to take her top off of her and in fact she would like that, but he didn't do that except with his eyes. She couldn't keep from gazing into his eyes. "Don, later, when this is over I'm going to tell you what I think has been happening. It just occurred to me that something is going on other than what I thought."

"I have all weekend to talk."

"I do too."

The phone rang again so Don just handed it to her. "Hello?"

"Have you fallen out yet?"

"I haven't moved."

"Well maybe this will get you to move. For your last part you have a choice. You can have Don take your top off or while you stand there have him reach up under your little skirt and have him take your panties off. Tell Don of your choices, I'll wait." She licked her lips and told Don of her options.

Don shook his head and whispered, "You don't have to do this."

"Logan I've decided that Don will remove my panties. Want me to tell you about it as it happens?"

"Yes that's exactly what I want."

"I thought you might but I'll have to put you on speaker."

"Okay."

"You are going to jack off while this happens aren't you?"

"I already am."

She set the phone down and said, "Don honey take my panties off of me please. Logan, Don's on his knees in front of me. His face is inches from my pussy now and his hands are slowly sliding up my legs. He's past my knees now...going up my thighs...he's touching my hips now...he...he's pausing for a second and his hands are feeling the front of my tiny thin panties. I can feel his warm touch through my panties. He has the top of my panties in his hands now."

Jan and Don were looking into each other's eyes but his hands on her were making her unsteady so she had to lean forward and put her hands on his shoulders. "Logan his touch is making me almost dizzy and I have to put my hands on him and lean forward for support...my breasts have just come free from my top and Don can see my hard stiff nipples. Oh my God his warm hands just brushed past my pussy. My panties are coming down now...down...down...they're...my panties are in Don's hands now Logan. I'm almost naked in front of Don now. Is there more that I have to do?"

"No nothing more."

"Oh...Logan, Don is taking my top off now."

"No that's not part of the dare."

"I'm naked to the waist. The only thing I have on now is my tiny skirt oh wait...oh yes Logan...oh yes,Don just took my skirt off and I'm naked in front of him now."