Jen & Me Ch. 4: And Jack...

Chapter 4: And Jack Makes Three

Ok, when I last put pen to paper my wife had encouraged me to have sex with her sister, and wanted me to get Jenny a boyfriend. I had some ideas there I was looking to test.

Oh, yeah. And my sweet little sister-in-law had talked Cheryl through her first anal experience. And to thank me for this, my wife was trying to get her cute-as-a-button best friend over so we could seduce her for a three-way, maybe a four-way if I could figure out how to work Jenny into it.

Damn, life was good.

* * * *

But I had responsibilities; that's why I had hit the gym early.

"Here's the deal, Jack. I think she's ready for a relationship; she hasn't had much luck with guys in the last year or two, which is good and bad. Good, because you're not going up against much competition, bad because she's currently going through an 'all-men-are-dicks' phase."

I had stopped by the gym, about an hour before I expected Jen to show up, so I could have a chance to lay some groundwork for Jack. He was number one on my list of potential suitors for my little Jen.

"I still can't believe she's not hooked up." Jack said, shaking his head.

"Yeah, part of it's gotta be working in bars and restaurants. The service industry is full of dicks - I know from experience. Listen, she's really into fit guys, so you have a leg up there." I went on to tell him what I knew about her pet peeves and interests. I told him about her favorite places, vacations, shows, and movies. Whatever I knew.

"She's not into a possessive relationship, but she wants monogamy. I don't know how to describe it. She'll play around, but only if you're there. Just no deceit, no lies - that will stop everything fast. I'd let her broach the subject. If you end up with her, let her bring up the idea of getting involved with others, don't you go there first." I warned him.

"Shit, are you serious? She might be into threesomes?"

"Whoa buddy, your first job is to seduce her. Convince her she's absolutely gorgeous. Respect her work ethic. Talk about futures, jobs, careers, dreams, and travel. Bring up Carnival in Rio, it's a dream of hers. Maybe discuss Spring Break. Go slow. She's not into a lot of physical contact, but I have a plan for that.

"Tonight, I'm starting her on an upper-body workout." I added.

"I'd like to workout her upper-body," he blurted.

"Yeah, and you may get your chance." I grinned. "I'm gonna ask you over as the expert, and you tell her that she's entitled to some free training lessons - since she never got hers, you'll work with her."

"She's been working out for a long time, why does she think she needs training now?" Jack asked.

"She's been into fitness training; now I've got her into body-shaping, trying to build her glutes, improve her abs, build her shoulders, and arms a little."

"Cool, we can do that. Man she'll be hot!" he blurted.

"I know. Now, some more stuff you should know. Keep this secret. Don't let her know you know." I was almost whispering.

"What, dude? Whatever you want, I owe you so big for this one." He joked, "I hope you didn't kill anyone."

"No, it's not that. She's not just a friend. She's my wife's little sister." I confessed.

"Are you shitting me? Damn dude, you're the man!" He threw up a hand for a high-five, which I grinningly smacked.

"Yeah, it all happened by accident, while I was trying to get back into shape and we were working out together for so long. You know, one thing led to another. But I think I'm in the way of her getting on with her own love life, so that's why we're here." I continued.

"So today, remember - lot's of friendly talk, tell her about her good features, and what we can do for her ass and shoulders. Don't hit on her. I'm going to lay some groundwork for that once she knows you a little. There should be a lot of touching, and if this works, I imagine she'll be hot as a firecracker when we leave her. I'll take her home and set up the next step."

"Jeez, I gotta go take a cold shower now, I'm getting a stiffy just thinking about her."

"You do what you have to do. I'm going across the street for a Smoothie, and I'll be back in 40 minutes for our 'workout'." I left him with a dazed grin plastered across his face. I hoped he could pull this off without giving the whole thing away.

* * * *

"Wow, Steve! I can't believe you got Cheryl to ask you to have sex with me. You are one manipulative son-of-a-bitch. I'm glad you're on my side." Jen was gushing from the moment she pulled up in her red Sunbird convertible.

"Believe it or not, she actually broached the subject. But I did play along. Since our sex life has picked up and she's lost all that weight, things are starting to get a little wilder than I ever imagined they would with her. Imagine her suggesting threesomes, or my doing anything with you." I was shaking my head in disbelief.

"She knows you love her. When you're sex life was so-so, she was really insecure, thinking you were tired of her. Now that you nail her three or four times a week, with some of those marathon sessions thrown in, she's more confident." Jen knew what she was speaking of; she'd always had a pretty open relationship with Cheryl.

"Now that she thinks it's her idea, she thinks she's the naughty one, and girls like that. She wants to coerce you to be with who she wants to share you with. It all sort of makes sense. Denise and I know a lot about your love life, and I think it's sort of like she's showing off for us. She wants to show us what she's getting all the time, and let us know she's not exaggerating. I know I'm a little jealous." She was grinning lasciviously, and she reached forward and put her hand on my cock, not so subtly, and licked her lips.

"Ok, Jen. Enough of that or we'll get the wrong workout done," I admonished. "Let's get in there and setup an upper body routine for you. Legs on Monday and Thursday, upper body on Wednesday, and one day on the weekend, Ok?"

"Ok, let's do it. Just don't kill me like you did last time."

"Come on, that didn't turn out so bad did it?" I grinned, patting her ass.

"You bastard. You'll get yours too." She giggled.

"I hope so, although I don't know if I can take much more."

* * * *

It was late enough that most of the crowd was gone. Since she'd switched to the new job, she'd cut back to just a few days a week, and one weekend day of working. She could work out evenings instead of mornings, and was seeing more of me.

I met her by the free weights section, and started telling her about what exercises worked which upper body parts. I stood her in front of the mirror, in her tight T-shirt and sexy short-shorts, and asked her what she liked, and what she wanted to change. She started bitching about most of her body.

"Hold on." I told her, "You really have a great body, we don't have to work everything. Just a sec. Wait here." I walked over to Jack who had casually worked his way over to our area. "You're on," I told him, sotto-voice.

"Jack," I spoke up, "come over here and help me, could you?"

"Sure dude, you need a spot? What are you benching now?" He played along.

"340 singles, 260 sets, but I'm not benching now. Jack, this is Jenny. Jenny, Jack."

"Sure, I know Jen, you and her have been working out here for a while - the queen of the bikes." He smiled.

Jen smiled prettily. "Hi Jack."

"Now Jack, we're going to do some body shaping here, what do you suggest. And don't hold back."

Jack walked around Jen, who was fidgeting. "Stand on your toes a sec, Jen."

She obliged.

"Ok, can you strike a biceps pose for me? Nice. I'm gonna lift your shirt to see your back and abs, is that Ok? Ok. Nice abs." He continued his examination.

"Mind if I feel your shoulders and arms?" He ventured.

"Go ahead." She was curious now, and trying to show off a bit.

"Hmmm. Well I'd say we need to work on the shoulders most. Most women like the wider shoulder look, and you are underdeveloped there. Your calves and legs are great, but you might want to pump up the glutes, to get a more rounded butt. Your lower abs and obliques are not as defined as your uppers, and your upper back and arms could use some definition. All in all, I'd say you look great, but we could probably have you in top shape in about 4-6 months of hard workouts. You have a lower body workout already? I saw you working out Monday."

Jen blushed strongly, and said, "Yeah, Steve got me on squats, dead-lifts and lunges. And he changed my ab workout to include legs lifts and twists. Today my poor butt is still killing me." She laughed.

"What is the best for her upper body, Jack? Incline bench, military press?" I inquired.

"No. No bench, her triceps need a little work, but we don't want to change a thing about her chest. That is pretty much perfect." He smiled.

"No, I'd say dumbbell work. Overhead press, upright rows, all three flys, and some light barbell curls for arm definition. With dumbbells, like all free weights, form is everything. In a month or two we might throw in some incline dumbbell press for the upper chest, just for muscle tone. Girls who are, uhh, 'well-endowed', usually benefit from the muscle tone in the upper chest. It keeps their breasts high and taut. But I don't think that's a problem here," he said, reaching out and rubbing the top of her chest, in an almost detached way. Damn, I should have had more confidence; this boy was good.

"Ok, I figure you never got your introductory three free training sessions, so I'll give you the next two weeks for free, just to get your form right. Let's head over to the dumbbell rack."

Jack worked her through the basic forms, and we did the exercises with her, each taking turns going through the motions, and feeling the muscles on the other, getting the motion just right.

Jack and I discussed her form, and commented on what was working, and what needed to be improved, sometimes almost as if she wasn't even involved. We'd feel her shoulders, arms and back a lot, even the lats near her breasts, without ever getting overtly sexual. But I could feel what this was doing to Jen, whose breathing was starting to get a little ragged. The tent in Jacks shorts matched my own.

When the upper body plan had been completed, and we'd written down a complete workout for her, Jack wanted to discuss her lower body workout.

"All in all, I think it's almost perfect. But I think she should use stiff-legged dead lifts. Here let me show you." He grabbed an Olympic bar, and demonstrated.

"Now you, Jenny." He told her. She did one, a little awkwardly.

"Not bad, but you have to bend over from the hips more, no arch to the back." He guided her through the motion, with one hand on her stomach, one on her back. "Do you mind if I touch your glutes? I want to show you where it will do the most good."

"No, it's ok." her voice was quivering.

"Ok," he placed his hands firmly on her cheeks, "I know your butt might still be sore from your Monday workout, but right HERE is where you should be feeling it. Now do one rep and concentrate on where I'm touching you."

Like he had to add that last comment.

"Oh, yeah, I see what you mean," Jen said, as she slowly worked through three reps in a row.

"Ok, good. Well that's enough for today, I'd say hit the showers and treat yourself to a Smoothie. Good workout, you've earned it. You are a really good student, Jen. You take direction well. And you work hard. You are going to look great - I mean, well you already look great, but you are going to be unbelievable. We may have to have you work out after hours so you don't distract all the other guys in the place." He laughed, and wandered back to the desk area, "I'll see ya later."

"Steve, we need to go to my place. Now." She was pressed against me talking softly, desperately.

"Yeah, I know. I wonder if anyone in here missed the obvious hard-ons both of us had."

"What hard-on? He was a complete gentlemen, and very professional."

"Oh, come ON. Are you kidding me, he was rock hard 5 minutes into the workout. You couldn't have missed it. You are a gorgeous woman and any man who was feeling you up like we were couldn't help but get excited." I told her.

"Are you serious? Oh my god. I never noticed. I was so horny I couldn't even think straight, It was like I had tunnel vision, I just let your hands guide me and did what I was told. I was even fantasizing about him making me suck your cock as part of the workout. You guys probably could have made me do anything 20 minutes into that session."

"Poor baby, I think I better take you home and let you work out some of your excess energy. Before I bust my shorts. Meet you at your place. Just grab your stuff from the lockers and head home, we'll shower after."

"Ok, I'll be right there."

My stuff was in the car; I didn't have to go back to the lockers, so I headed to the front, and Jack.

"Perfect Jack, she is so hot right now, we could probably screw her here in front of everybody and she wouldn't object. You were great."

"Jesus, I kept trying to think of baseball and Mickey Mouse, but I couldn't get rid of my hard-on. So what does she think?" he asked.

"She's intrigued. I think we're going well here. I'm going to take her home and douse the fires; then I'll see what I can find out. I'll let you know."

"Dude, you are great. Thanks, man."

"No sweat, see ya later." I headed out, straight to her place.

* * * *

Jenny came into the house, walked right past me and headed straight for the bedroom, stripping along the way. "Are you coming, or what?" She demanded.

"Here," I handed her a homemade smoothie, "Your post workout drink."

"Mmmmm, pretty good, what's in it?" She asked after polishing off a third.

"Creatine, glutamine, fruit juice, and vodka." I smiled at her.

"Vodka? Now that's part of the regimen?" She took another sip.

"No, but I was hoping to loosen you up so I could have my way with you," I teased.

"Well, today's your lucky day. For the next few hours I am your love slave. Use me. Use me hard. God I need to be fucked right now." Jen polished off her drink, and stood before me, removing my shorts.

Once my shorts were off, she stood before me, looking into my eyes. "Tell me what you want. Anything."

"Ok. Go get a broomstick." I told her.

"Why?"

"Do it. Don't ask questions, do what you're told." I snapped at her.

She hurried out and returned with a mop handle.

"Good, now I want you to show me your starting dead lift position." I took the handle from her and placed it across a couple of books on the floor.

Jen took her wide stance. Legs straight. She bent over from the hips, her back almost parallel to the ground in order to reach the handle.

"Good, now hold that position, chin up." I walked around her. "No wonder we had hard-ons, what a great DP position."

"DP?" She asked.

"DP - double penetration." I stopped in front of her, tilted her face up, opened her mouth, and placed my hard cock in it. "See perfect height." Holding her head, I fucked her face a few times, then pulled out, and stepped behind her. I placed the head of my cock in her wide-open pussy, and grasping her hips, shoved it in to the hilt. "See, wide open, easily accessible." I pulled out and pushed it in harder, rocking her on her heels.

"Yeah, when Jack was holding your butt while you did this exercise, I could just barely resist whipping out my cock and feeding it to you. Remember my tilting your head up to make sure you kept your posture right?" I was now working my cock slowly, very slowly, in and out of her pussy.

"Yeah," she answered softly, remembering.

"Well, I could see Jack staring at your ass, his hard-on about one inch from your butt. I thought for a moment that he might rub it up against you. You had him sweating. Ok, now hold that position a little longer." I pulled out and walked over to her closet where I pulled out her bag of toys. I was behind her as I found what I was looking for. I stepped in front of her, holding the nine-inch dildo.

"Here, get this wet for me," I told her, sticking it in her mouth.

Once she had moistened about half of it, I walked behind her. "Oh look, it's Jack, and he can't resist that gorgeous rear any longer." I stuck the dildo in her tight pussy, and slowly worked it in. "Oh he likes this sweet young thing. So pretty, such a little hard body, so good at taking directions." I had almost the whole thing up her by now.

Jen was very quiet. She was breathing heavy, but even her moans were contained.

Leaving the dildo shoved up her cunt, I walked around in front of her. "What's that you say Jack? Why, yes I do think it's a shame that such a pretty mouth should be unoccupied. Why thank you, don't mind if I do." I held my cock in front of her, slick with her own juices. She opened her mouth wide, tilting her head back making a direct path down her throat easily accessible.

"Say Jack, have you seen how talented her mouth is? She's a good student and has really worked hard at being an expert little cocksucker. Why don't you watch her take my entire cock? Yep, every inch." I was working my cock in and out of her mouth, and started pushing my way in deeper. Soon I had her nose in my little remaining patch of trimmed pubic hair. "Look at that Jack," I said, holding her head while I fed her the entire shaft and held it there. "Every inch." I pulled out, letting her catch her breath. She was cheating a little, resting her hands on her knees, but maintaining the position.

A few moments later I was back behind her, this time with her chrome vibrator out. "What's that Jack? Oh yeah, it's a pretty sweet little butt-hole. Shame that it's empty. Well, yeah, I don't imagine she would mind." I turned the vibrator on and started rubbing it against her little brown opening. I alternated between licking her hole, doing my best to shove my entire tongue up her ass as far as I could, and diddling her ass with the vibrator.

Her legs were trembling badly. I thought it was time for the second part. I pulled the big dildo out of her pussy, and straightened her up. Leading her to the bed, I lay back, still holding the dildo and the vibrator. I placed them to the side. "Ok, Jenny, show Jack how well you've learned your squats." Jen placed a leg on each side of my waist and slowly lowered herself. I held my cock straight up and she took it to the hilt in her pussy. Then she raised and lowered herself onto my cock, fucking me ever so slowly. "Yeah, I think so too, Jack, perfect form. No, please go right ahead, I have no need for her mouth at the moment," I said, as I passed her the dildo which had been up her pussy for the last five minutes.

Jenny dropped to her knees, and started rocking back and forth on my cock, while she closed her eyes and demonstrated the long hours of practice she'd probably had with that big cock in her mouth. When I started fucking her harder, she took almost the entire thing down her throat. "See what I mean? Yeah we are lucky." I reached up and took the dildo from her, then pulled her against my chest.

"Yeah, I think she's ready for it. Go for it buddy." I reached behind her with the vibrator, and by feel, started working it in her butt. "Of course it's tight, you're her first back there, and I'm already inside, filling half the available space." Jenny was finally starting to moan louder, and to stop herself she was chewing on my shoulder.

"Ok Jack, I agree, lets fuck her ragged." I was fucking her hard from below, and working about 4 inches of the vibrator in and out of her ass. She was biting me hard, her fingernails digging into me. Her breath was gasping and suddenly I could feel her coming, her pussy clenching at my stiff cock. She was squealing into my shoulder. I turned the vibrator from low to high, and held it deep in her ass, as I fucked her as hard as I could from below. She was slamming her cunt down onto me. I reached over to her head, pulled her off my shoulder by her hair, placed her mouth over mine, and stuck my tongue half way down her throat. I could feel the end coming and finally pulled the vibrator from her butt, as I unloaded a huge amount of cum inside her. With each stream I lifted her several inches off the bed. On the third lunge she tore her face off mine, arched her back and screamed as a huge orgasm shook her body. I reached up and squeezed her erect nipples, as the final remnants of my own orgasm finally subsided.