From Scared to Dared to Bared to Shared: The Next Semester 03

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After that night at the Candy’s party, Jay and Kate spent the day together, mostly in bed and alone. Jack and Lisa were out for the afternoon, Karl would be returning later in the evening, so they could make love without an audience for a change. Kate remarked on this novelty, and that started a conversation on all they had done in the last year.

“Just think,” Kate reminded him, “it all started with us girls letting everyone see our underwear. And if you hadn’t let Cindy and me take yours all the way off, well, who knows what we might never have done.”

“No nude beach,” Jay said. “I’d have missed that a lot.”

“Being nude isn’t the only thing we’ve done with others.”

“You have second thoughts about any of it?”

“No, but a year ago, if you told me that I’d enjoy having two boys inside me at the same time, and that you wouldn’t be one of the two, I’d have laughed if I didn’t slap you.”

“And now?”

“Now, if you suggested it, I’d be almost looking forward to it.” Jay laughed at her eagerness, and Kate added, “Not that I don’t love this kind of time with you. In fact, you’re the one I have the easiest and best orgasms with, and I’d like that to stay the same forever.”

Jay agreed, “Me too,” and they resumed their play. Only later when she was getting ready to leave did Jay ask, “Is there anything we haven’t done that you want to try?”

“What would that be?” she wondered.

“I don’t know, but it just occurred to me to ask.”

A short time later, as if to confirm that she was still the sexually daring girl she’d been over the last year, she didn’t react when Karl’s key was heard in the door. That is, she calmly remained nude in front of the bathroom mirror, drying and combing her hair when Karl walked in. She even gave him a quick hug in greeting when he came to the bathroom door, and he could continue to enjoy looking at her as she was gathering her things to go.

After Kate was gone and Jay was back from the bus depot, where he saw her off, Karl got the summary of the weekend’s events. Cindy and Steve could give the same report to Amy and then to Ted, so all the friends had heard the whole story before long. Or at least, they had heard all the story except for the last bit

of Jay’s play in the shower with Candy. He had told Kate, but no one else, and Cindy was keeping it to herself too.

As for Kate, she liked the idea of Jay being played with, but she admitted to him that she had not that much interest in putting her fingers inside him or any other boy. At the time, she laughed, “Maybe a bat inside Sean. I’d do that, but not my own fingers.”

Because Kate had not raised any kind of new play she thought they should try, Jay was not thinking of anything new either. Cindy, on the other hand, was thinking a lot and keeping it to herself. “You have a hole to play with too” stuck in her mind, and she decided to explore the idea more. If Jay wasn’t considering something new to try, Cindy’s exploration was about to give him something new to experience.

Cindy would have involved Steve first, if things had worked out according to her plans. Steve’s new job and the time he had to work didn’t necessarily upset those plans. Later, she could look back and know that her teacher’s careful instructions had unconsciously upset those plans.

Cindy was in the office of her Sexuality Studies teacher from before, Mrs. Brookner. “I have a question for you,” she shyly started.

Mrs. Brookner immediately replied, “You can look up at me. No question is so bad that you have to look at the floor when asking.”

Cindy then met her look and said, “One time in class last autumn term, you were talking about so-called perversions.” Before Mrs. Brookner could interrupt, Cindy went on, “You said that, for the most part, there are no perversions when adults are simply giving pleasure to each other.”

Mrs. Brookner was pleased and said, “That’s right.”

“At the time, you also mentioned how some couples can kind of trade places.” Cindy stopped to see if Mrs. Brookner recalled the class session.

“Yes, what is it you want to ask about that?”

“I maybe should have taken better notes, but I think you and the textbook referred to a thing for doing that. I wanted to know more about that thing.”

“Ah, you’re wondering about a strap-on, is that right?” Cindy hesitated again, hardly able to imagine she was talking about such a thing with a teacher. Mrs. Brookner did not hold her reticence against her. “You seem embarrassed to be asking, but I think you’re showing your open-minded attitude, the healthiest attitude you can have when it comes to questions of sexuality. So you want to know about a strap-on. So what? You look like a young woman who knows her own pleasures and knows how to pursue them responsibly. In fact, coming to me with this question is only another sign of that responsible thinking. So, please, tell me how I can be of help.”

“I remember that you said some people almanbahis get frustrated because they can’t get things they want privately. You said that, if sex toys were available in a way that people didn’t feel they were losing privacy, then more people would enjoy more pleasures.”

“And you want to know how to get such a toy without having to go to a seedy sex shop with a leering clerk. I can help. I know the mail order place, and I have many such items delivered to my home often. And not all for me, not at all. You’re not the only one who comes to me with these sorts of questions. Being a college professor, I have the luxury of being thought of as a researcher, so the questions are natural, and as for the packages, even if someone knows about the deliveries, I don’t get the same gossipy treatment others might get.”

“So I can get one from you?”

“Get what? If you’re going to play with a toy, you should be able to call it by its name.”

Cindy sat up straight and asked again, “Can I get a strap-on from you?”

“Yes, I would be happy to help you.” She handed Cindy a slip of paper with an address on it, and she said, “I know I can get the delivery by this time next week, so why don’t you come to my house that evening, say around eight o’clock.”

“Okay, but I’ll need only one, right?”

“Oh, I like to order different designs to give you choices, you know, different shapes and sizes. I will have what you want, the others will be extras that I can use or let others have.”

“Okay, I’ll see you then.”

“Good,” Mrs. Brookner answered. “Oh, and be sure to bring your friend.”

When Cindy had left the office, she wondered about that last instruction. She recognized the name of Mrs. Brookner’s street and knew it was near campus and in a nice neighborhood. Finally, she just figured Mrs. Brookner was being careful that she not walk alone at that time of night.

At the time in Mrs. Brookner’s office, Cindy didn’t ask to change the time of the meeting the following week. She knew that Steve would not be available because of his job, but Mrs. Brookner had told her to bring a friend, so Cindy thought anyone would fine. As it turned out, Jay was the one she met just inside their apartment building after returning from Mrs. Brookner’s office, so he was the one she asked. He was happy to go along without even asking where or why they were going.

If Jay didn’t ask for clarification from her, Cindy did not even know she should have asked for clarification from Mrs. Brookner. The next week, with Jay accompanying her, she did bring up her purpose in going. “You’re going to see what I get from my professor, so I might as well tell you now.” Jay was intrigued, of course, and she went on, “I’m getting a strap-on from her.” She said no more, letting that statement hang.

“Oh, yeah, you mentioned that one time before. So what made you decide to actually get one.”

“I saw how Candy made you come a second time in the shower.” Again, she let that statement hang.

“Yeah, that was something alright. So you’re thinking of being able to use it on Steve and not other girls?”

“No set rules for it, I think. Girls and boys too, maybe, but it was pretty hot the way Candy put her finger inside you. Just made me think, that’s all.”

Having told Jay what their trip was for, she still did not know what Mrs. Brookner’ instruction to bring him along meant. When the two of them arrived at Mrs. Brookner’s home, the talking at cross purposes continued.

At the door, Mrs. Brookner greeted Cindy and turned to Jay, saying, “Why, I think I recall you. Aren’t you a former student of mine? It’s Mr. Jay, right?”

Jay was just as surprised to see her, saying, “Yes, you taught my Intro to Psych class. I didn’t know you were Cindy’s professor too. I’ve heard a lot about the class she took with you.” He didn’t go on, realizing he should not presume to know too much, but Mrs. Brookner thought it was natural he would know all about it, because she assumed Jay was Cindy’s boyfriend.

“Well, I’m glad to see you again. Not my best student, but an attentive one, as I recall.”

Jay didn’t want to admit that attending to her was easy because she was so pretty to look at. The tight skirts, the blouse with two or three buttons left undone at the top, and occasionally the resulting peeks down her blouse at her lacy bras were all brought back to Jay’s mind. He was partially aroused already from talking to Cindy about the shower with her and Candy. The sight of Mrs. Brookner even more casually dressed did not help. Her skirt was shorter than she would wear in a class, and her blouse was a wrap-around style that exposed a bit of midriff and fastened on the side just above her waist. Not that tight, it gaped slightly over her cleavage. He made himself not stare, but he also had the impression that the way her blouse moved was an indication that she wasn’t wearing a bra.

Cindy asked her, “What do I owe you for it?”

“It? almanbahis yeni giriş I thought we were not being coy anymore, young lady.”

Cindy blushed a little and rephrased her question, “What do I owe you for the strap-on?”

“We’ll get to that later. For now, we need to take some time to be sure you know what you are doing. We don’t want anyone getting hurt, of course, but we want to make certain that you know how a strap-on can bring the most pleasure to both of you.”

“Oh, he’s not-” but Mrs. Brookner had turned to lead them into another room at the back of the house. Cindy and Jay followed, noticing a man in the living room as they passed by, presumably Mr. Brookner. He was wearing a robe with an exotic Asian design and satiny sheen. Reading a book, he looked up only briefly to acknowledge them.

The room in the back was a guestroom, and the sheets on the bed were turned down. Before Cindy could say anything, Mrs. Brookner told the two of them, “You’ll want to get undressed now.”

Her tone was so matter of fact that Cindy did not immediately reply. When she could gather her thoughts, Cindy started to explain, “We aren’t, I mean, we weren’t expecting-” but Mrs. Brookner cut her off again.

“I take my responsibilities very seriously, and I don’t want you two going away without some lessons. I assumed that you wouldn’t be embarrassed about getting undressed since you weren’t embarrassed about approaching me to acquire a strap-on and ask me about its use. Was I mistaken?”

“No, I really wanted to get your advice and all, but-“

“That’s all I need to know. Now, let’s proceed. You cannot learn what I can teach you with your clothes on.” Cindy looked at Jay, and Jay gave her a shrug as if to say it didn’t matter. She understood him to mean that they had been naked together often enough and had even had sex together, so it really didn’t matter in that sense.

Slowly then, the two of them began to undress. For Cindy, taking off her shirt left her quickly topless. Mrs. Brookner smiled and said, “I thought you did not wear a bra. That’s good, a nice way to stimulate your breasts during the day. I wish I could do the same when teaching, but I think the deans would disapprove.” As she spoke, her attention shifted back and forth from Cindy to Jay, observing his gradual exposure.

The phone rang, and Mr. Brookner came to the room’s door just as Cindy was about to remove her panties. He gave her an appreciative look, even though he must have seen this sort of thing before. Cindy, of course, did not expect such a casual attitude, and her surprise only grew when she noticed that his robe was not fastened, allowing her to see that he was otherwise nude. He had a bit of a tummy and a long, flaccid penis. Under the circumstances, Cindy found herself pulling down her panties right in front of him and then facing him nude as if expecting the phone message was for her. He gave her another look up and down before he told Mrs. Brookner who was on the phone, and then he was gone with instruction for the callers to come to the house in an hour.

Jay was also nude by the time Mr. Brookner came by, and the interruption had distracted Mrs. Brookner. With the phone call taken care of, she could turn to him and take a look at his body, making no pretense and ensuring that he knew she was checking out his nudity from head to toe, even telling him to turn around once.

“Very nice, Mr. Jay. I think when someone sees another person’s body, partially or fully nude, even if by accident, it is a privilege. And I am grateful for the privilege of seeing both of you. You are both very attractive. Cindy, if you were surprised by my husband’s seeing you, you can be assured too that he feels privileged as well and hopes that you were not offended by his nudity.”

“No, not at all,” she replied, although she was taken aback by the incident.

Mrs. Brookner returned her gaze to Jay’s penis and asked, “May I?” Neither Cindy nor Jay knew what she was asking, but both nodded. Mrs. Brookner said, “That privilege is especially treasured when, with a boy, his penis is erect. The boy is then sharing himself most intimately. For now, though, I also need to look at yours because I need to see what size we are dealing with already.” With that, she grasped his penis and stroked it. He was already nearly erect when he took off his pants, so his full erection was soon evident. “Just as I would have guessed from my first look, about seven inches and moderately thick. You can take a place on the bed now.” Turning to Cindy, she said, “I’ll be back in a moment.”

Left alone briefly, Cindy started to apologize to Jay, “I had no idea this would happen.”

Before she could go on, Jay interrupted and said, “You’re naked, I’m naked, so I can’t say I’m not enjoying this. In fact, I’d say it’s a privilege.” Cindy smiled at this, and they both had an inkling of what was going to happen by then, and they were willing to stay rather than stop almanbahis giriş everything by explaining to Mrs. Brookner that he wasn’t Cindy’s boyfriend.

They did not have time to discuss the situation more as Mrs. Brookner returned with a small box of items. “Let me show you how I like to start. Mr. Jay, if you will get on the bed and scoot down to the edge and roll over on your stomach, we can begin.”

Jay did as asked, and he was then sure of what was coming. Mrs. Brookner said to Cindy, “I like a boy’s bottom to be hairless like this. It looks so innocent and vulnerable when turned up so cooperatively.” She was lightly touching his bottom as she said so. Speaking more to Jay then, she added, “And I applaud you for being so open-minded, Mr. Jay. An inviting and cute bottom means nothing if a boy does not have a willing nature. Your willingness to experiment will lead to much pleasure for you and your lover.” Jay turned to her, and as she bent toward him, he got his first clear look into the gap of her blouse. Mrs. Brookner was indeed braless, and her one C-cup breast was exposed completely. She knew and did not care. In fact, she knew it would enhance the experience.

Reaching into the box, she took out three items. To Cindy, the most notable of the three was a flesh-colored phallus that pretty nearly matched the dimensions of Jay’s. In fact, Mrs. Brookner took it and, grasping Jay’s erection, held the fake penis next to Jay’s. “Just as I thought, about the same.”

It was attached to a complicated looking belt. Mrs. Brookner noticed Cindy’s consternation and said, “It looks difficult, but don’t worry. Let me help you get it on correctly.” She showed Cindy how to hold the larger belt open and step into it. As Cindy did so, she noticed the inside of the small patch that would go over her own vagina. It was not only contoured to fit smoothly between her legs, it had a protruding piece with a knob about the size of a large grape. Mrs. Brookner said, “This piece goes over and inside your vagina. Pushing the phallus inside your man will be more stimulating if there is something also pushing inside of you.” Cindy held the belt as Mrs. Brookner adjusted it to fit her waist, and then, when adjusting the straps around the tops of Cindy’s thighs, she gave the patch a firm push into Cindy’s vagina. Cindy grunted a little, but she smiled when Mrs. Brookner checked to see that she was comfortably adjusted. “You look like a pretty woman with a natural penis now. Before you put it to use, you have some preparation to learn. That’s what these are for.”

She was holding up a tube of lubricant and smaller phallus that had no straps. It was black, and its size was closer to a long finger than to an erect penis. “Before a boy can comfortably accept a full-size penis or phallus, his anal passage needs lubrication and gradual stretching. This smaller phallus can do both. To my way of thinking, the chief advantage to having this second phallus is that you can use it with your hand and not have to insert your own fingers in the boy’s anus. That way, there’s less time lost to washing hands or putting gloves on and off. With this, once you start playing with your boy’s bottom, you never have to pause and start over.”

Mrs. Brookner was offering the tube and smaller phallus to Cindy. “Take it. I want to see that you learn how to lubricate it and Mr. Jay’s bottom.” Turning to Jay, she said, “Let’s have you lift that bottom just a bit,” and she grasped him around the waist to help him get into position. Reaching underneath him, she brushed his hard penis as she used her hand to adjust his position even more by pressing up on his stomach. “Mr. Jay is still ready in at least one way, I see,” she laughed.

Cindy meanwhile was putting lube on the smaller phallus, and Mrs. Brookner advised her to be more generous with it. “Not a thin coat like paint. More like jelly on a peanut butter and jelly sandwich. But leave room for your hand to hold it firmly.” When she was satisfied that Cindy had coated it sufficiently, she showed Cindy how to handle it. “Place it against his anus. It certainly is nicely red, so you won’t have trouble finding the spot.” Cindy did as instructed. Jay found the lube to be a suddenly cool feeling. He, of course, did not have expectations based on previous experience, so everything was a surprise in a way, which contributed to him feeling a bit nervous on top of being excited.

Mrs. Brookner continued, “That’s right, let it rest against his anus. By itself, it will be slippery enough to slide around a little, which is what you want. Once his anus is well surrounded by the lube, you can begin to work the phallus inside slowly and gently.”

Cindy was trying to be gentle already. As much as she wanted to add a strap-on to her sexual abilities, she was conscious of Jay’s inadvertent presence in this lesson. Even so, she proceeded as instructed, and the ease with which the tip of the phallus could enter Jay surprised her. Jay, of course, was equally aware of having his anus invaded, and he was surprised too at the ease. Cindy was encouraged, and after a silent nod from Mrs. Brookner, she pushed it in further. Now Jay was getting a sensation that was more than Candy’s finger had given him.

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