It Runs in the Family Ch. 02

Author's note: Chapter 2 deals extensively with crossdressing. So if that is not something you enjoy, you might want to skip this one.

It Runs in the Family

Chapter 2- Friday

Sheila slept in rather late the next morning. She briefly awakened when Les got up to go to work. She remembered him bending over her and kissing her goodbye.

"Well looks like this could be an interesting night," he said.

"I think it will be," she replied.

He reached down and traced a finger around one of her nipples. Sheila had not bothered to put any clothes back on. It had been well after midnight by the time she got to sleep, quite exhausted from all the previous day's excitement. When Les left, she dozed off again. When she once again opened her eyes it was after nine.

Throwing on some shorts and a t-shirt she headed downstairs, curious as to the whereabouts of her son. The house was silent, and when she got to the refrigerator she saw that Marc had scribbled on the whiteboard that he had gone for a run. She poured herself a bowl of cereal and got some fruit and sat down at the breakfast table, turning on the television, idly watching the Weather Channel. It looked to be another warm day with little chance of rain, with highs in the mid 90's. As she sat and ate, she began to formulate the other half of her plan. If things went according to plan, Les was in for a more interesting night than he imagined. Now she just had to arrange the rest of her fantasy. There was also an entire day to think of. She had several lustful ideas in her head, but she would have to wait for Marc to get home to put any of them into practice.

Marc was still not home when she had finished with breakfast, so she threw some dishes in the dishwasher then headed upstairs and changed into a pair of tight jeans and one of her white lacy bras, which she covered with a pink tank that accentuated her cleavage quite well and left little doubt about the shape of her hard nipples. She also slipped into a pair of platform clogs which did for her ass what the plunging front did for her breasts. By the time she finished dressing, she heard the garage door open and close and knew Marc had returned from his run.

When she descended the stairs, she found him in the kitchen, shirtless and quite sweaty, a big glass of ice water in his hand from which he was taking large swigs. The clinking of her clogs alerted Marc to her presence as soon as she hit the tile floor at the base of the stairs. She was watching his face closely as she entered the kitchen, looking for signs of how he felt. From the smile, and the way he was already staring at her chest, she suspected he was not having any misgivings about what had gone on the previous day.

"Have a good run, Son?" she asked.

"Really good. I did nearly six miles."

Sheila smiled, sat down at the breakfast table, admiring his almost hairless chest and flat abs. Already she was having to exercise some control to keep from ravishing him then and there in the kitchen. But there was much to be done that day. She took a deep breath and began to implement her plan.

"Well I talked to your father last night," she said, jumping right into it.

Marc's smile faded a bit. He took another drink of water then set the glass down on the counter, then leaned against it, as if he might need some support.

"So how did it go?"

Sheila leaned forward over the table a bit, staring her son in the eyes, a reassuring smile on her face.

"It went fine. Your father was not upset at all."

She could see him visibly exhale.

That's good," he said. But he remained where he was. He knew there would be more to it than that.

"In fact," she continued, "he only had two requests."

Marc looked a little nervous again now. She continued to smile and motioned for him to come sit down with her at the table. When Marc was seated, she continued.

"First of all, we both agree, that you have to stay out of our room."

Marc nodded, the smile completely gone now, his head dipped a little bit. He had sort of been expecting that.

"But," she quickly added, "we both have no problem with you wearing women's lingerie."

Now Marc's gaze returned to his mother's face. "Uh, okay," he said. She could tell the wheels were turning then. She suspected this was not something he had expected. "In fact," she continued, "your father suggested that perhaps the two of us should go shopping for some today."

Her son squirmed a bit. "I don't know Mom. Don't you think people would stare at me in a women's lingerie department?"

"How have you been getting them up to now."

Marc smiled sheepishly at his mother. "Online, mostly."

Sheila nodded. She should have known Marc was too shy to buy it in a real store.

She leaned forward even more, her breasts almost spilling out of her top. "No one would think anything of it if you were with your sexy Mom. Especially if you acted a little bored, like you were being forced to do it."

Marc thought about it for a moment. "Yeah, I guess that's true."

Sheila sat up straight once more. "Then it's settled. You go get cleaned up and we'll head down to the mall, then come home and have a little lunch."

Marc nodded. He noticed some twitching going on in his groin. He stood up, was about to head to his room, then stopped.

"What was the other thing?" he asked, suddenly remembering.

"He wants to see you all dressed up."

Marc's mouth dropped open. Sheila waited to see if it signified shock or embarrassment or some mixture of the two.

"Really?" he asked.

She nodded. "Really. He just wants you to truly see that he understands. Besides, he said he bet you would look really sexy in a teddy."

Now she could tell that her son's mind was really reeling. It was obvious none of this had ever crossed his mind- or had it? For suddenly, the worried look changed to a smile, almost a grin.

"Sure, okay. I guess that wouldn't bother me too much."

Sheila stood. "Good. Then it's settled."

Marc started to walk away, then stopped once more, turned back to his mother.

"Are you sure Dad is okay with this?"

She smiled. "Oh I think he's actually more than just okay with it. "

Marc gave her a curious look and she knew he was thinking about that one. But soon his smile returned. "Then I guess I am too," he said.

Sheila stood, leaning back against the table, absently running a finger down her neck then gently sliding her middle finger between her cleavage then pulling it back out. Marc watching the whole time, no doubt wishing it was his finger doing that.

"Good, then let's go have some fun."

Around ten they headed for the mall. Normally this was only a fifteen minute drive, but unfortunately they got stuck in one of the all too common traffic jams along I-25. Seeing that they would have some time to talk, Sheila decided to do a little more probing. She was so horny she could hardly stand it, just thinking about what had already happened, and what she hoped was going to happen later that day. She decided to start out with a little teasing, just to loosen things up a bit.

"So you really think your Mom is good looking, do you." She glanced across at him quickly then looked back at the road.

"Yeah, Mom. I really meant what I said yesterday. You're the most beautiful woman I've ever seen."

Sheila chuckled. "Now surely some of those young girls you've dated were more attractive to you than your old Mom."

There was no immediate answer, and when Sheila glanced over at her son, he seemed a bit embarrassed, his eyes looking at his feet. After perhaps 15 seconds or so, Marc began to talk.

"To be honest Mom. I've never really done anything with any of them. I've made out some, and once I played with a girl's tits, but I never took it any further."

Sheila found that hard to believe. Perhaps she was a little prejudiced like all mothers, but she knew her son had a healthy appetite for sex and as good looking as he was she found it hard to believe that some girl had not jumped his bones by now.

"So you're saying you're a virgin?" she asked.

Marc managed a feeble, "yeah." After a pause he added. "I just wanted the first time to be with someone special, and I haven't found that person yet. I guess I was sort of looking for somebody like you only younger. But most of the girls I've met so far are just silly and vain."

Now Sheila was getting exceptionally aroused. She knew what she had in mind for her son would be a totally new experience, but she had no idea it would be this new.

"Hmm," she said, thinking out loud now. "So yesterday I was the first woman you had ever seen nearly nude?"

There was another awkward pause, which she quickly assumed meant one thing.

"It's okay if you've been to a strip club, son. Nearly all young boys do that."

Still no reply. Finally, after a few more seconds of silence, she heard him take a deep breath. "No, it's not that." He paused once more then said. "Mom, if I tell you this will you promise to keep it a secret?"

Sheila had to laugh. "Son. After what we did yesterday don't you think you can tell me anything and trust me?" She gave him another quick glance, saw him looking at her, his lips pursed.

"Yeah, I guess so."

She returned to her teasing voice. "So who have you seen naked besides me? Mrs. Frasier?" Mrs. Frasier was the 50 something lady who lived next door to them. She was a bit plump but very attractive for her age, and Sheila noticed that she sometimes sunned topless in her back yard. She had enormous breasts- much larger than Sheila's, and lovely ivory skin, a dark head of hair.

This managed to get a little chuckle out of Marc, easing the tension. "No Mom- well, I did see her sunning by the pool once without her top. But that's not who I'm talking about."

"Then who was it?"

More silence, then another deep breath.

"It was Kim." There was a slight pause. "And that's not all."

What followed was a scene that shocked Sheila, but in a strange way did not surprise her. Kim had never been shy about her sexuality. Mother and daughter had always had a good relationship. They had talked about safe sex and more than once Kim had mentioned a boy or two she had dated that had "impressive hardware" as she put it. They had never gone into great detail, but Sheila knew her daughter was as vivacious as her son was shy. But Kim had never mentioned anything about Marc that indicated in the least that she looked at him as anything but the typical yucky little brother. As they slowly crept along in the traffic, Marc told his story:

"It was a couple of summers ago. Kim had come home for a few days after she graduated from college. One day you and Dad had gone to some sort of concert in the park for one of those old groups that we didn't have any interest in."

Sheila nodded. She vaguely remembered that. It was a cover band for some hair band, but she couldn't remember which one for sure.

"Anyway, you guys told us you were going to be gone all day and then go out to eat that night so Kim knew you guys wouldn't be home for quite some time. I had been for a run and had just gotten back. I had thrown my sweaty shirt in the hamper then headed for the kitchen- sort of like I was this morning. When I came in the kitchen she was sitting there drinking a beer. She seemed to stare at me longer than usual, and she had this sort of odd grin. But I didn't think much about it. I said hi, then headed for the fridge to get some cold water. I got a big glass full and downed it quickly. As I set it down on the counter I looked over at her and noticed she was still looking at me. I wondered if my fly was open or something, but it wasn't. I got another glass of water and then sat down across the table from her.

"So what do you have planned this afternoon little brother?" she asked me. She was wearing a halter top and some white shorts, and I could tell she didn't have a bra on because her nipples were sticking out. In fact, they seemed bigger than I remembered them being. Anyway, I told her I was going to shower then probably watch some golf- they were playing the U.S. Open that weekend.

She stood up then stretched her hands above her head which made her boobs stand up really nice. "Sounds pretty boring to me," she said. "I think I'm going for a swim. I've got a new suit I want to try out." Kim always spent a lot of time around the pool in the summer, so that was no surprise. She turned to leave the kitchen, then stopped for a moment, and said, "you might peek out the window and tell me what you think of it."

I just sort of shrugged at the time. "Sure," I said. "Whatever."

But after she left it got me to thinking. She had never done anything like that before. I headed for the shower, and what with the warm water cascading down my body I started getting a little horny. I had never really thought about Kim sexually, but I knew she was good looking. Now I found myself thinking about what she might look like in that bikini. I tried to push it out of my mind, but it kept coming back. I was even getting a hard-on. I threw on some gym shorts and headed for my bedroom. I looked out my window at the pool, but Kim wasn't there yet so I turned on the TV and settled onto my bed to watch some golf.

About ten minutes later I heard the back door shut and saw Kim heading for the pool. As soon as I heard the door shut I went to my window and looked outside. She was wearing a brown bikini with little flowers on it. It looked okay, but it was nothing special. I was thinking she might have gotten a thong or something. But like I said, by this time I was kinda horny so I kept watching her for a while. After a minute she turned and faced my window directly. There is sort of a glare there so I figured she couldn't see me so I was staring at her pretty hard.

She reached up behind her head and made her tits stand up real nice. She had a serious look on her face, but then she got this little smile. The next thing I know, she moves her hands right to her tits and starts rubbing them. Then it got really interesting. Next thing I know she reaches between her boobs and pulls them out of her suit. My eyes nearly popped out of my head, and my dick was getting really hard. She started to run her hands all over her tits, then started to pinch her nipples. After a bit, she reaches behind he head and takes off her top and tosses it to the side. Then she turns around and pulls off her bottoms, and points her ass right at me, then turns around and faces me completely naked! She had shaved all around her pussy, just leaving a thin little strip.

Then she headed over to the pool and jumped in and started paddling all around, and jumping up out of the water from time to time making her boobs bounce really nice. After a few minutes, she swims over to the edge of the pool and just leans her boobs over the edge of the pool, looking back at my window again. Then she climbs out of the pool and heads for the lounge chair. She had brought out a towel with her when she came, but I hadn't really paid much attention to that. Now she reaches down to the towel and unrolls it, and there's a glass dildo inside of it! She dries off then lays down on the lounge chair which faces right towards my window. She spread her legs apart and I could see her pussy lips really good. Next think I know she is taking the dildo and sticking it between her tits, looking at my window the whole time. Then she begins to lick the head, lubing it up I guess.

At this point my dick was hard as a rock so I just threw off my shorts and started stroking it slowly. I wasn't even thinking about her like my sister at this point. It was just some incredibly hot girl, laying by my pool with her pussy lips spread.

Then she took the dildo and began inserting it in her pussy. She slowly worked it deeper and deeper, faster and faster, while rubbing her clit.

He stopped for a minute then, and when Sheila glanced over at him, he said. "She's got a pretty big clit too."

Shelia smiled. So there was something else that ran in the family as well. Wait until he got a look at mine, she was thinking. She tried really hard to keep her eyes on the road so they didn't have an accident. She was so wet below she was afraid it might soak through her panties.

"So anyway," he continued. "After a few minutes I could tell she was coming. I was stroking my cock really fast, not even using any lube, and about the time she closed her eyes and started cumming, I shot a big load all over the little table in front of the window."

Just then they pulled into the mall parking lot. "So what happened then?" she asked.

Marc shrugged again. "Not much really. Later that day when she passed me in the hall, she said, 'Well, I hope you enjoyed your golf as much as I enjoyed my swim,' then winked at me. I was so embarrassed I just nodded and headed to my room. We never said anything else about it again."

Sheila's mind was really working overtime. She had been fantasizing about her and Marc, and Marc and Les, and even about the three of them. But Kim was going to be home sometime around noon on Saturday. That could make for a really interesting weekend. If Kim was willing to do that, Sheila suspected she was willing to do quite a bit more with a little encouragement. Who knew what the weekend might bring? She tried hard to control her emotions as they pulled into a parking sport.

"Okay son," she said. "Let's go pick out some lingerie."

There were several shops that had lingerie, but there was just one that she felt a need to enter-Victoria's Secret. For one thing, they would have the best selection. Secondly, it was not that uncommon for women to drag their boyfriends or husbands into there. Chances were Marc would not be the only male in there. Approaching the entrance, they noticed a mannequin modeling some red lingerie in front of the store. They stopped for a moment and looked her over.

"What do you think?" Sheila asked. "Is that the sort of lingerie you like."

Mark looked the mannequin up and down a couple of times. From the time he was taking, Sheila suspected that he actually had opinions on the subject, as if this was not the first time he had contemplated the multitude of styles garment makers had created to make a woman look sexy.

"It's okay," he stated. "But I like teddy's and bustiers better. And I like them with more lace and trim and kind of sheer."

Sheila smiled. Marc, so far, did not seem too nervous at all. In fact, now that they were here, he seemed quite excited. They had devised a simple system by which they could communicate about what Marc wanted for himself without giving away what they were actually doing. If she showed him something that he didn't like, he was to shrug his shoulders and say, "It's alright I guess." If he saw something he really wanted, he was to scratch his head, and say "whatever."

Now, standing in front of the mannequin, Sheila shrugged her shoulders and said, "It's alright I guess?"

Marc smiled. "Exactly," he said.

"Well," she said. "Let's go do some shopping then."

Inside the store were more mannequins and half mannequins modeling all sorts of styles. Sheila went towards one of them that had a cute little set of black crotchless panties and a beautiful lacy babydoll top that was also rather sheer." Marc came alongside her and gave it a critical look over. His shyness seemed to have disappeared almost altogether.

"So what do you think of this one?"

With little hesitation, he scratched his head, but instead of the code word, he just smiled and nodded. Sheila looked at her son, trying to visualize his cock stuffed into those little panties, his hairless chest showing off the babydoll top. "Well, maybe I should get this one," she said to him.