Michelle

“Sounds like she liked to rob cradles. Kind of like what I feel like right now. Why wouldn’t she let you fuck her as a special little-brother favor?”

“Well, as the next day proved, that was something she just could not have conceived of handling psychologically. Obviously for her it was – and is, I guess – a big taboo. But it might have crossed her mind. Or maybe just all the sex talk and dope and alcohol had turned her on a bit because she suddenly decided we had to go swimming to ‘cool off.’ Well, it was a hot night too.

“The problem was we hadn’t brought our swim suits. I was perfectly willing to swim in my underpants, and Jen would swim in her panties, but she was just wearing a tube top and she didn’t want to come back to the raft and sit around in a soggy wet top afterwards. She made up her mind she was going to swim topless and she told me so. I tried to sound casual and cool – ‘yeah, whatever’ I said, or something like that – but my heart was pounding out of my chest.”

Michelle said, “Oh yeah, this is sounding like what I called for. My nipples are so hard now. And I’m gliding my hands are skating on the baby oil up and down my stomach. And sometimes … like now … I just let one of my hands slide under the waist of my pantyhose and gently – very gently – tease my clit. Oh that’s good. C’mon, Jamie, I want you to start caressing Jennifer’s tits for me – you know she wants it.” Now Michelle was definitely breathing more audibly.

“No, I don’t think she did want it. She kind of took her top off with her back to me and dove into the water before I could see much. We swam for a while and then I got back onto the raft first. I now had an urgent hard-on and I didn’t want Jennifer to see me, so I was lying on my stomach when she came back to the raft. But she asked for my help in hoisting her up. I kind of came over to give her a hand, hiding, as best I could, my too obvious excitement about her being topless. But as soon as she got on the raft she took one look at my underpants and started giggling. ‘Jesus, Jamie, look at you. You could house a family of refugees in that tent you’ve made out of your underpants.’ Meantime, of course, she was still standing there topless. And even though it was pretty dark, I could see the dark patch of her bush through her wet white panties.

“Anyway, I sat back down and lay on my stomach again. My face was burning. And though she probably couldn’t see that in the dark Jen obviously sensed my embarrassment and tried to make amends. ‘Come on, Jamie,’ she said, ‘it’s no big deal: boys get hard-ons. And I know I didn’t help by being topless. I’m sorry.’ And she started to put her top back on. ‘No, please.” I pleaded. It was out of my mouth before I thought about it.

‘Please what?’

‘Please can I look just a little longer?’

She looked at me and softly said, ‘Okay.’ And she just sat there with her hands at her sides letting me study her breasts. She had spent the previous summer in Europe where I know she had gone topless at the beaches (I’d seen photos). So it wasn’t a big deal for her, but she realized it was a big deal for me. She was very sweet about it. Like I said, she’s a good sister. I think she was also pleased that I found her sexually attractive. ‘Are they nicer up close like this, Jamie?’

‘What do you mean?’

‘I mean when you’re spying on me you’re always a distance away.’

‘Spying?’

‘Jamie, don’t think I haven’t noticed you spying on me. Trying to see me nude. You might someday notice that there’s a mirror in my room that I can see who’s in the hallway without turning around.’

‘Well maybe I was just passing your room.’

‘No one takes that long to pass a slightly opened door. It’s not a big deal, Jamie – every younger brother spies on his sister. Karen said she’s caught David about five or six times. And he even admitted one time that he masturbates picturing her.’

‘Cut it out, Jen.’

‘Why? Do you jerk off fantasizing about me?’

I didn’t know what to say. Well I wanted to say no, but, of course, I did fantasize about her so I was kind of frozen for a second. Jennifer correctly interpreted the hesitation.

‘You do, don’t you! Why you wicked little boy, you.’ When she said this she reached out and sort of pushed me on the shoulder.

‘Leave me alone!’ I said and I rolled away from her. Of course when I did this I once again exposed my standing-tall jockey shorts. But by now I was more mad than embarrassed so I just lay on my back with my arms crossed staring at the stars. Screw her I thought.

‘I was just teasing you, you know that don’t you,’ Jennifer said kindly. But then she started giggling again.

‘What?!’

‘I’m sorry, Jamie, but I just saw your erection again and how incredibly stiff it looks. I’ll bet you wouldn’t last half a minute with a girl.’

‘Shut up,’ I said, “Wha’do you know?’

‘Well, when it comes to sex and teenage boys, I know a helluva lot more than you do. I bet you wouldn’t last a minute masturbating.’

‘I would too!’ And it went on like that. It wasn’t any conscious strategy on my part to get her to give me sex, but in the end, almost before either of us realized it, that was the bet. She bet she could get me off in under a minute.

“I know this makes no sense, Michelle. But remember, first that we were stoned, and second, that at one level it was just a sibling argument and we each wanted to prove the other wrong. We even haggled over the details. She had a sports watch she used for swimming and she took it off and gave it to me. I said that the clock would start running whenever I said ‘go.’ She said no, that it would start the moment she first touched my dick. ‘When you first feel my hand on your cock,’ she said, ‘then you say “go” and push the start button on the watch.’ After a moment I agreed because I felt this was a minor concession; I had no idea how aroused a woman could get you without ever coming into physical contact with your dick. I also made the mistake of thinking that Jennifer was a girl – I mean she was just my sister, right? Wrong. Somewhere in the five years between us she had become a woman. I just hadn’t been paying attention.”

James paused in his narrative and he could hear Michelle breathing very raggedly now. Despite Michelle’s prohibition he started stroking himself more earnestly. Prompted by the pause in the story, Michelle said, “In case … you … can’t tell, Jamie … I’m getting close.”

“How close?”

“Close. Just tell me how she got you off? Was she good?”

“Oh yes. She was good. First she said that I had to take my underpants off. She moved down to my feet and then, while being careful not to touch my cock and thus start the clock, she reached up, put her fingers under the elastic band at the waist and very slowly pulled them down to my ankles. My dick popped free, bounced and then came to rest at about a 45-degree angle pointing toward my chest. Jennifer then took some sun tan lotion out of the bag she had brought the towels and the blanket in. She smeared it slowly and suggestively all over her hands while I watched.

Her eyes were devouring my cock. ‘Oh my baby brother has such a big cock,” she said. ‘I love the way it curves up like that. It’ll make some women very happy some day. Oh I can hardly wait to see it spurt.’ Remember I was fourteen. I had never had a woman talk dirty to me. And, in fact, my cock wasn’t all that big –”

“How big is it right now, Jamie? And stop jacking it. I can tell by your breathing that you’re cheating on me.”

James had been caught, but he didn’t cease his stroking, he merely slowed down. “Okay, okay, I’ll stop,” he lied, “And to answer your question: bigger than it was then, but not porn-star size. Right now though I gotta say it looks very big … and reddish-purple and glistening.”

“Glistening? Do you have baby oil too?”

“No, I produce this stuff myself.”

“Oh it sounds so beautiful I’d love to see it.”

“No reason why you shouldn’t. I’ll make my offer again.”

“You absolutely can’t, James. Or I can’t. But please just get me off now. What’d your sister do, rub that suntan lotion all over that cock.”

“No, not then. But Jen knew very well what she was doing with her dirty talk. She was still sitting –”

“Wait! Does it still curve up?” Michelle interrupted.

“Yes.”

“Oh God, you don’t know how I love an up-curve cock. Go on.”

“Well, still sitting at my feet, she slowly leaned forward and reached for my cock with her hands all slick and lotiony. I closed my eyes in anticipation of the feeling. But her hands stopped instead at the tops of my thighs. And then tantalizingly slowly she began caressing my legs and my inner thighs. I realized then that I was going to lose this bet. In fact I thought I might even lose it without the clock ever being started. I opened my eyes then and watched Jen leaning forward over me and sliding her hands up and down my legs. She was looking deeply and sensually into my eyes, all the time talking softly (‘Do you like this, Jamie? Come on, you can admit it. Isn’t it nice having a sister with soft hands to protect you from the sun with this lotion? I know there’s no sun right now, but you can never be too careful. You just lie back there and know you’re being taken care of. Is there anyplace else you’d like me to protect?). She probably could have talked me off.”

James could hear Michelle almost panting now.

“Close?” he asked her.

“You … know … I am,” Michelle said between her labored breaths. “Your sister … better get you off in a hurry … or she’ll miss the … boat.”

“Well every time Jen moved her body forward to massage my thighs with her slippery hands, her breasts would sway forward toward me. She must have noticed that I was mesmerized by them because she suddenly changed tactics. She got some more lotion on her hands and she slid herself around above my head. Then she started massaging my chest and gradually moved her hands lower to my stomach and abdomen, still being careful not to touch my dick. But because she was behind me, now when she would lean forward now, her breasts were positioned right over my face. And a few times she scrunched down so that they brushed my cheeks and nose and even my lips. God, I didn’t know what to concentrate on, the fire that was building in my balls or these wonderful soft breasts caressing my face. Jennifer was acting like the breasts were just an accidental by-product of the chest and abdomen massage, but she was careful to make sure they dragged tantalizingly across my skin. At one point she leaned way down to rub as far as my pelvis bone and she pushed her breasts into my face and held them there for a few moments. I reached up with both hands and gently stroked the sides of her tits. I was moving my hands forward toward her nipples when she abruptly sat up and took hold of my wrists, putting them back by my sides. ‘No copping a free feel, or you don’t get anything. You understand, you dirty little boy?’ And she totally stopped everything. This drove me wild. I begged her. ‘Please start again, Jen, please. I won’t touch you.’

‘Well, okay.’ She was totally toying with me now and she started rubbing my chest again and teasing my nipples. ‘Are you ready to start the watch?’ Oh yes, I was very ready. Finally she touched me and I started the stop-watch. I was expecting her to grab my stiff cock and start piston-stroking it. But instead she gently ran her hand up my member and then wrapped it around, squeezed, and started slowly stroking, all the time talking. ‘Oh Jamie, you’re sooo hard. Are you ready to cum for me? Cum for me now. Make it shoot, Jamie.’ And then with a groan I let go. ‘Oh God, Jamie!’ Jen said excitedly. ‘You’re cumming. Jesus, I’ve never seen anyone cum so much. Wow!”

James stopped his story there and was now seriously stroking himself. He could feel himself on the edge and he knew Michelle wouldn’t stop him this time because he could tell she was almost there herself. She was having trouble breathing and she was whimpering. “Oh plesepleaseplease --- OOH Yes, now!! I’m cumming! I’m cumming. I’m cumming.” Sometime during the pleases James had shot his load. And now in their aftermath both of them were quiet and listening to each other catching their breath.

Finally, Michelle said, “Whoa-baby. Oh, James, thank you, thank you. I really needed that. There were a few moments there when I pretty much lost the plot, but I’m assuming you joined me.”

“Oh yes, Michelle. It’s very much of a mess here right now.”

“Do you really shoot so very much jizz, James? Like your sister said?”

“I guess I do. I mean at the time I didn’t have any basis for comparison, but Jen seemed very impressed. I mean, as I told you, she never mentioned a single thing about that night after that, but that night she told me that I had looked like an oil well gusher and it had shot up as far as my chin. Since then, several women have made comments of a similar nature. Jennifer was so wowed by it she forgot to even check the time it had taken her to get me off until later. When we finally did check, the stop-watch was still running. I had totally forgotten to hit the stop button. There was no argument about who won the bet though, even I had to admit that I couldn’t have lasted more than maybe twenty-five or thirty seconds tops. Jen looked at her right hand and laughed at what a sticky mess of tanning lotion and cum it was. She started rubbing it off on my chest and then on my wet underpants. I was too weak to resist. I did thank her though, and I told her I’d never forget this. But she told me I’d better forget it. I guess she was already starting to have regrets about what we’ve done. We both lay back on the raft and were in our own thoughts and then, like I said, the next thing I knew was the sun coming up and the Bradleys in their boat coming out to see if everything was all right on the raft.”

“James, it’s almost 3:30. I’m going to have to go to sleep. I’m forty-six, you know, I can’t stay up as late as someone your age.”

“If you could see me right now you’d see that I can’t stay up either. My cock looks pretty tame right now.”

“Well, good night. And thanks again for every thing. For the help with the show. For the pot. And for taking me over the deep end just now.”

“Thank you too, Michelle. See you at ten tomorrow morning. Good night.”

* * *

Michelle had her team together at ten to go over plans for the next two days of the conference. There were six of them and she reviewed responsibilities and gave out assignments. James took notes, but his mind was on the previous night and marveling that this high-powered, tough-talking producer was just a few hours ago whimpering and pleading for him to get her off. It made her seem so incredibly sexy to him.

As the meeting was about to break up, Michelle asked if she could have a word with James after the meeting. When the meeting room emptied, Michelle walked over and closed the door. James, whose cock was already stiffening in anticipation, had started walking over to touch her when Michelle turned around with a hard look on her face.

“Stay away from me, James.”

“Well, sure. What’s the matter?” said James, taken aback by her tone.

“About last night. I’m going to ask you to totally forget about it. There was drinking. There were drugs. I was letting my hair down from the pressure of the show. It all got very much out of hand. Some of those things should never have happened. And I’m going to ask you to give me your solemn promise that you will never breath a word of any of this or any of the things I told you about myself to anyone.”

“Michelle, what’s happened? I mean it wasn’t just you that shared confidences.”

She took a deep breath and angrily said, “Look, James, I don’t intend to have a big discussion with you about this. I simply want you to promise me.”

“That sounds like you’re ordering me.”

“You can look at it that way.”

“This is the woman that just seven hours ago was pleading, pleading with me to get her off?”

Michelle turned around abruptly. James could tell from the reddening of her neck, the set of her shoulders and her clenched fists that she was furious. Finally, she turned around and in a strained but controlled voice she said, “Look, it’s different for you than for me. For you, it’s just a young guy, wild oats, sweet talks his boss into having a bit of phone sex, shoots his rocks, so tell me a new story. For me, it’s my career. Do you understand that, James?”

“Yes, I understand. I guess I’m just a little disappointed that you don’t trust me. That you think I’m the kind of person that would –”

“I’m feeling very vulnerable here, James. I mean if it ever got out that I once blew three guys through a glory hole. That I had phone sex and flashed my cunt at a 22-year-old boy. A boy who works for me for Christ’s sake.” She shook her head in disbelief at the position she had put herself in.

“Don’t worry, Michelle,” James reassuringly, “your secret – or secrets – are safe with me.”

She looked relieved. “Thank you. Will you swear to that – that you’ll never say anything?”

“On one condition.”

“What’s that?”

“Nothing much. It’s just that before I’ll swear to keep my lips sealed for life, you have to open yours and give me a blow job. Fair trade, huh?” He looked at her and smiled.

Stunned and angry, Michelle stared at James. Neither said a word for several moments and then James saw tears welling up in Michelle’s eyes. His expression changed to concern and he came forward to hold her, but she pushed him away so forcefully he almost fell over a chair.

“Michelle, please! I was joking. Honestly. I thought you could see that. I wouldn’t do that. Look, I’ll promise anything you want – no conditions. Just don’t be upset, please.”

Michelle looked at him and believed.

James said, “I promise never to breath a word about the glory hole or the phone sex or the fact that you don’t wear any panties under your pantyhose. I swear.”

“Really?”

“Really.”

“Thank you,” she said. “Boy, when you said that about me giving you a blow job I was just thinking, ‘God, what he must think of me.’”

“You want to know what I really think of you? I think you’re a great producer and a superwoman. Strong and talented. Easily one of the most impressive people I’ve met in the business so far.”

“I appreciate your saying that more than you’ll ever know, James.” She said it sincerely, but then she added with a laugh. “But last night you also mentioned a ‘hot bod.’ What happened to that part, huh?”

“True,” James kidded her back, “I guess I can add that. It’s not one of the three things I can never mention again.”

Finally Michelle said, “Hey what are we doing around here? We’ve got shows to put on.”

* * *

Over the next day and a half, Michelle’s unit was kept very busy helping out at various individual seminars and break-out sessions, moving equipment, running equipment, setting up stages and taking care of all the usual backs and forths and mini-crises that accompany any major conference. In between all this Michelle had scheduled several rehearsals and technical run-throughs for the big show the last night of the conference.

Michelle rehearsed the client Vice-President of Sales – a good-looking man of about fifty named Damon Whiteside – on his speech, which was then to be followed by the most extravagant, glitzy segment of the entire conference. It involved a magician making the Vice-President disappear and then re-appear in the back of the room. It involved a laser/light show, a small fireworks display, hard-pounding rock and roll music, dancers, balloons and confetti raining down from the ceiling, even a disco ball (“trite, but tried and true,” Michelle had said with a laugh of the ball).

James worked with Michelle through out that next day and was with her much of the time. But she seemed distant with him – more business-like and no-nonsense than she had been even in the weeks prior to the incredible night before. At dinner Michelle sat with the VP-Sales instead of at the table with her team. This was not wrong – she was supposed to establish a relationship with the client, but it bothered James.