Sometime Sweet Sheila

Sheila adopted several elegant dance poses. She obviously had taken some ballet lessons along the way she hadn't told me about. I looked like a drunken scarecrow when I tried to mimic her. She seemed to enjoy her dominance over me in a good-natured way. It had been several minutes since she last covered her boobs.

"Let me do something easier, James. I see you're having trouble following my lead. Can you touch your toes?"

With some effort and a lunge, I could.

"How about this way?" She sat down on the floor, extended her legs in front, and easily grabbed her toes.

I got down with her and tried, barely making contact. "Can you grab your heels?"

She could. I couldn't even get close.

"How about this?" Sheila easily lowered her elbows to the floor while still holding the soles of her feet. I was astonished she was that flexible. There was more to come.

"Let's see how your upper body strength is. That's where men have an advantage." She rolled over into a prone position and lifted up her entire body horizontally, bearing the weight on her palms and the edge of one elbow. I could barely do a push-up.

"Too tough? Let's try an easier one." She put her palms on the floor, intending to spread her legs wide and lift herself up.

She couldn't quite do it. Hah!

"Damn! Not with these pants on. Hold on a sec."

She jumped up and had her jeans past her knees and off in a flash. Nice little white cotton undies with lace trim appeared. A minute before I had no idea how I was going to convince her to shed any more clothing, but now her pants were on the floor. She sat down, spread her legs as wide as they could go, and lifted her entire body weight on her hands.

"There we go. Should be easy for you."

No, it wasn't. Remember what I said before about not working out. She had strength in her shoulders and back that I'd never seen in a woman before.

"How about a handstand split then?" she asked.

She did a handstand and lowered both legs horizontally to turn her body into a perfect letter "T." I gave it a try but toppled over.

"Nice effort, but don't try that on a balance beam, OK?"

"You have my word." As long as she was showing off, why not ask for another risqué pose? "Vertical split?"

"I think I can still do one." She hopped to her feet.

The next thing I knew, she was standing on her left leg with her right leg perfectly upright: behind her head, toes pointed at the ceiling, left hand clasping the sole of her foot, and the other on her shin.

"Sheila! My god, how can you do that?" Her little panties barely covered her pussy.

She laughed. "Willpower."

All her poses were insanely erotic. The female body in all its youth, grace, and flexibility. Her statuesque height only added to the effect.

"OK, just one more. I don't want to make you feel too bad about not keeping up with me. Another naughty one?" she asked with a coy grin.

Back down on the floor she went, flat on her back. She lifted her pelvis up and rolled her whole lower body back until her knees touched the floor near her shoulders. Her arms were draped over her calves, fingers touching her heels, panties tight against her upturned rump. I was stunned—it was beyond naughty.

"Not finished yet," she bragged. She rolled her whole body forward and had her heels behind her head and touching. "Ta-dah!"

"Sheila, I concede! Magnificent. You are the champion. I can't believe how flexible you are. I've never seen anything like that. Except on television. Well, not that last pose. That one got my attention."

"Thanks," she said, returning back to her starting point. "I thought it would."

We were both on the floor, breathing hard. She from exhilaration, me from exhaustion. The vibe in the room had shifted. I could tell by the look in her eyes. She seemed to have conquered the embarrassment of having her top off—and then some.

"Sheila, I think the bed may be more comfortable than the floor." I helped her up.

We started kissing on our way over to the bed. She seemed more relaxed and receptive than before. My hands roamed all over her almost naked body and through her hair.

"You have the most beautiful hair. I can't keep my hands off it." It looked a bit disheveled after our workout. She must have spent some effort in getting it to look just right before our date. "Sorry, I didn't mean to mess it up."

"Mess it up all you want."

The look in her eyes when she said that! My erection went from hardwood to steel. And on top of that, I realized I was overdressed. "I suppose it's only fair I reveal the color of my underwear now."

"I think you should."

"Can you undo my belt, please?" I wanted to push her to be less passive. "Remember, we agreed that's as far as we're going with our disrobing."

She smiled. "Right. I remember."

"I want you to feel safe here with me."

"I do."

Sheila fumbled around trying to get my belt buckle undone. I wondered if she'd ever done that for a man before. After sitting down on the bed and yanking off my jeans, I motioned for her to come closer and stand in front of me.

I pulled her toward me and began stroking her ass and hips. A soft groan encouraged me to keep going. I drew my lips across her tummy and teased her navel with the tip of my tongue.

"Oh, James."

I continued to kiss her torso as I moved my caresses farther up, along her back and sides. My thumbs roamed near her nipples, pressing and stroking all around her areolas.

"That feels so good, James."

I let my tongue tease one of her nipples.

"Yessss! More!"

So I gave her more: gentle sucking, rough tongue teasing, hard sucking. A tug with my lips, a soft bite. Mouth on one, fingers on the other, switching back and forth. She ran her hands through my hair as her legs became unsteady.

"Can we lie down now? You're making my knees weak. In a good way."

Onto the bed we went. "Are you comfortable now?"

"Yes."

"We'll only do things you're OK with."

"I trust you."

We began kissing as we lay on our sides facing each other. Sheila's response was more enthusiastic than before. Her hand wandered over my body, matching the caresses I was giving her. After several minutes of kissing and stroking, I got up on one elbow.

"Can you roll over on your back?"

I wanted a broader area to touch. My hand glided around her body—breasts, tummy, and hips. Over her thighs and across the front of her panties. She groaned when my fingers teased her mound. Her hands seemed unsure of where to touch me, so I placed them on her breasts.

"Show me how you like to be touched."

She moaned and closed her eyes, moving her hands slowly over her boobs, lightly pinching her nipples between her fingers. I resumed stroking the front of her panties and the soft skin between her thighs as I observed her self-pleasuring.

I moved up onto my knees and bent over to fondle her hair and kiss her more deeply. My other hand cupped her entire pussy and gave it a squeeze. Her panties were very damp. I massaged that area slowly, feeling her twitch against my palm.

I whispered in her ear, "Touch me like I'm touching you." She opened her eyes and gasped. "Go ahead. Feel how turned on I am. From being next to you like this."

I took her hand and guided it to my boxers, which were soaked with pre-cum. I placed her fingers around my erection. "See how hard you've made me already. You know, men get wet, too. If they see a woman that drives them wild. That shows how sexy you looked in the mirror."

She seemed tentative and not sure how to touch me, but she didn't pull her hand back. She moved it around a little.

"That feels nice. Do you like how I'm touching you?"

"Yes," she said softly.

I was still unsure where her head was at. Was she shy? Scared? Uninterested? I decided to change things around.

"Sheila, why don't you roll over and get up on all fours? I'm going to keep my underwear on, but I'm going to rub up against you." She moved into position without a word.

"Spread your legs some more. OK, good."

Sheila's head was hovering above the pillow, her hair a sexy mess. With my cock still covered, I pressed it against her panties. A tiny moan escaped her lips. I moved around a little, but it felt way too good. I needed to be cautious or else I'd fill my shorts with the groaning reservoir of cum that had been dammed up for hours.

"Does that feel nice, Sheila?"

"Mmmmm. Yes."

I felt a little stirring underneath me as she began to move around herself. I let her set the pace. Her arousal grew steadily.

"Oooh, James!"

We fell into a slow, sensual rhythm. Two thin pieces of fabric keeping our animal parts from joining, per our agreement, but allowing sweet sensations to pass between us.

"Keep doing this?" I asked.

"Yes!"

Less than a minute later she cried out as a spasm shook her body. She dropped to the bed, face in the pillow and a hand between her legs.

I moved down beside her. I wasn't sure, but it seemed like she may have had an orgasm. I stroked her back and kissed her shoulder as she lay on her stomach.

"Sheila? Are you OK?" She turned her head to look at me.

"Did that feel good?"

"Mmmm, yes."

"Did you come?"

"I'm not sure ..." She closed her eyes and reconsidered. "No, I guess not."

I eased myself up onto one elbow and continued to caress her. She rolled over on her side and looked at me.

"I was getting close. But it startled me. I wasn't used to it."

"Have you had sex with a man before?" Never too late to ask, I suppose.

"Yes."

"With a boyfriend?"Please let it be a boyfriend.

"Yes, my high school boyfriend."

"How was the first time?"

"Not that good. It hurt. He was more ready for it than I was."

"Was it better the next time."

"A little."

"Did you have orgasms?"

"No."

"Did it keep getting better?"

"Not really."

"Well, you were both inexperienced."

"That's for sure!" A long pause followed. "He broke up with me after we did it the next time. And started dating another girl at a different school. She had a reputation for being fast."

Sheila had a sad look on her face. "It felt like I gave it up for nothing."

"Did you date anyone else after that?"

"The timing of the breakup was awful—right before the senior prom. I had to scramble for a new date."

"Who'd you end up going with?"

"I asked this geeky guy, a junior. We grew up in the same neighborhood. He'd been tutoring me in math that semester so I could pass.

"He accepted it as a one-time situation. I didn't dump him when I got there or anything like that. We danced together—despite my towering over him. I wanted both of us to enjoy the evening. My friends didn't give me a hard time about it. They understood. They're not mean girls."

"I don't suppose you—"

"No," she said, laughing. "A goodnight kiss was more than he was expecting. Anything else probably would have caused a heart attack."

"Did you find someone else that you liked well enough to sleep with?"

"Not until later."

"Someone from your school?"

"A guy visiting for the summer, a cousin of one of my friends. We got drunk, and I let him do it. It turned out to be a one-night stand. He never called me again.

"And I was always nervous about getting pregnant. Even though both of them wore a rubber each time. I know they aren't foolproof."

Surely, she must know what an orgasm feels like from masturbation. I guess I could ask.

"Do you get yourself off when you're alone?"

Sheila let out a burst of embarrassed laughter and rolled over on her back. "I can't believe you just asked me that."

"OK then, I'll go first. You can be thinking about your answer. I confess: I definitely get myself off when I'm alone. If you weren't here now, and if I had gone to those movies by myself, I'd already have made myself come at least twice.

She finally admitted to diddling herself. "Am I actually telling you this?" she moaned, covering her face with her hands.

"Sheila, this is a night for learning and talking and comparing. So, you know your own body well enough to make it happen by yourself?"

"Yes ... I can. But both guys finished too quickly. And they never bothered making it nice for me. I don't know, maybeI'm not doing it right."

She turned on her side to face me and touched my arm. "That's why I wanted to see the movies tonight. I thought it might help. The two people I went to bed with—neither of them seemed like they enjoyed it enough to keep dating me."

"Did you learn anything useful from the movies?"

"Oh, yes! More than I could imagine! Too much. I don't know how I'm going to be able to figure it all out."

"You don't have to do everything at once, you know. I think it's commendable that you wanted to learn. It took some courage to go to those movies. And with someone you didn't know that well. But you seized the opportunity to seek out that knowledge. To make it more enjoyable when you're with a man."

I had an uncontrollable urge to go down on her at that point. It could freak her out at first since I was almost certain she'd never been pleasured that way. But I was betting she'd quickly get over that. After all, the movies showed some very convincing scenes of cunnilingus and the women who enjoy it.

"I'd like to make it nice for you, Sheila. Tonight. You deserve that. All women do. It shouldn't be a one-way thing where only the man has a good time. Would you like for me to make it nice?"

She smiled. "Yes, please do!"

"Let me do something for you that you can't do for yourself."

She seemed puzzled. "Like what?"

"Here, sit up. And I'll lie back down. OK, now crawl on top of me. Yes, straddle me. No, you're not too heavy. Up on your knees a little. Move up closer to me."

She seemed unsure about how things were going to work or what exactly was going to happen. I caressed her hips.

"I going to make itvery nice for you, Sheila."

I slipped my hands between her thighs and rubbed both thumbs against her panties.

"Ooh! That's a good start."

I crooked my finger past one leg of her panties so I could pull them aside and touch her pussy with my other hand. As soon as my fingertips grazed her labia, she began whimpering. Oh, was she slick and wet! I teased her lips until I thought she was ready for more.

"Move a little closer to me."

She inched forward and groaned when my finger went up inside her. Her nectar oozed out onto my hand. I dipped into her several times to get that "almost orgasm" warmed up again. Sheila was grabbing and kneading her breasts roughly.

I pulled my finger out and spread the wetness over her labia and clit. Her head went back as she stifled a scream. Time to announce my intentions.

"I want to kiss you. Where my finger is right now."

"No! ... I'm ... I've never done that. I'm not sure I ..." Her hands fidgeted. "I may not be OK there ... not ready."

I knew she didn't have a string hanging out—and it wouldn't have mattered to me anyway.

"You're not on your period, are you?"

"No, but—"

"Look at me, Sheila."

I pulled my hand away from her kitty and put it in my mouth. Her eyes widened as I licked her arousal from my fingers. Her taste drove me wild.

"You are more than ready for this. I can't wait to make you feel good. Didn't the women in the movies look like they were enjoying it? Let me make love to you like this."

I inched closer so my lips could touch hers. I used the hand that was holding back her underwear to spread open the silky blonde hair around her flower and eased two fingers inside her.

"Oh, my god!"

I started licking—slowly, gently. She shuddered as my tongue danced around her clit.

"Mmmh! Oh, fuck!"

It hit me almost as hard. My senses were overtaken by the rich scent of her musk and a gentle hint of the Yardley perfume from her thighs.

We quickly fell into an urgent rhythm: her gyrating against my mouth while my fingers and tongue brought her closer and closer to the end. Damn, she tasted good. Sheila seemed nervous as her orgasm approached, but her pleading said otherwise.

"Don't stop, James. Oooh, that's it. Keep going. Keep going. Oh, god!"

Sheila grabbed my head moments before letting out a long wail. She thrashed about as a raging climax tore through her body. Struggling to catch her breath, she sounded as if she were choking and crying at the same time. Strong contractions clenched my fingers as I thrust them in as deeply as I could.

When her orgasm eventually tapered off, I stopped licking and brought my fingers to rest. My face was damp with her release.

Sheila slumped over me, hands on the bed. She was shaking and moaning. I let her calm down a little.

"I'm going to ease my fingers out of you now, OK? I'll be gentle." A little sigh of disappointment followed.

She seemed stunned by what had happened. I wriggled free and moved next to her trembling body. She was on her knees and forearms with her face pressed into the pillow. I leaned over and caressed her.

"Sheila, honey, lie down now. I want to get close to you."

She eased herself down on the bed. I did the same.

"Can you lie across my chest?'

Her eyes were half closed as she crawled on top of me, put her hand on my shoulder, and rested her cheek against mine. Our other hands intertwined as I hugged her tightly, feeling her wet pussy on my hip. Holding her so closely at that moment caused unique sexual sensations to spread through my entire body. I was surprised at their intensity. I stroked her hair and let her recover. She shifted around a little and let out a contented sigh.

"I'm guessing that was your first time? On the receiving end?"

"Yes, it was. That's definitely something I could get used to."

"Sheila, I enjoyed it as much as you did. You may not understand that now, but I did."

"Hmm, I've never thought about it that way. I guess that was one of the messages from the movies tonight. Giving pleasure brings pleasure."

She raised her head and gave me a thankful look.

"That's the first time I've ever come with a man. It felt so good I almost couldn't handle it," she confessed. "I think it was the rush of emotions that went with it. It was so unexpected, based on my other times."

"It means a lot to me to be your first. You had to trust me enough to let yourself go."

"I did. I'm glad I did."

She kissed me gently but passionately, unafraid to taste herself. That got me even hotter.

"Do you want me to do something for you?" she asked. "Make you come?"

Oh god, yes! My balls felt like they had been in a vise for the last two hours. I didn't want to push for oral—too much too soon. A hand job would do just fine. All it would take was a few strokes, and I'd be wetting the ceiling.

"I'd love that. You can use your hands on me."

"OK. I know I saw a lot of that in the movies tonight, but will you show me howyou like it done?"

"You bet. Sit up and lean back against the wall. Put some pillows back there. We'll sit face to face while you touch me."

We got into position with our legs spread open. I scooted up close and draped her legs over mine. I needed to come so badly I was ready to faint. I pulled out my cock with my boxers still on and placed her hands on it.

"Stroke me. It won't take that long. I'm about ready to burst."

She smiled and tentatively handled my cock. I realized that was likely new territory for her.

"Have you ever made a man come with your hands?"

"No, I didn't need to. It was skirt up, undies down, jam it in—and over before I had a chance to think about it. And never face to face. I like the way we're sitting now."

"There's nothing to it. Remember in the second movie where she jacked him off using both hands? Let's try that."