Jenna Makes Her Move

BACKGROUND

Jenna has been our babysitter for many years. When my wife and I first moved into the neighborhood from out of town, we had a 6-month-old baby boy. Recognizing the importance of reconnecting as adults now and again, without having to keep a careful eye or ear on the baby, we wasted no time trying to find someone who could baby-sit. We struck gold almost immediately.

Our next door neighbors told us about the Stewart family, who lived down the street. Krista Stewart had babysat for their children, who were much older, and they knew that Krista's younger sister, Jenna, was just entering the babysitter market. At the time, Jenna was only fifteen years old. Her youth made us uncomfortable, but we decided to call her anyway on our neighbor's recommendation.

What a great move! On the phone, Jenna presented herself very well. She was well-spoken, polite, and generally seemed quite mature. And she was just as impressive in person. We arranged for Jenna to baby-sit for a few hours in the afternoon while my wife was home, just to keep an eye on her and see how she handled the baby. It did not take long for us to conclude that she was completely responsible and capable. Thus began a successful babysitting relationship.

Over the past several years, my wife and I welcomed a baby girl, so that we now have two children ages five and two. Jenna is still our primary babysitter, even though, at the age of 19, she now attends a community college across town. As you might expect, she is almost like one of the family at this point.

Although I am happily married and almost forty myself, I cannot help but wistfully admire how Jenna has grown into a beautiful young woman. She has long, dirty blonde hair, large brown eyes, healthy, blemish-free skin, and an athlete's physique. Her breasts are slightly smaller than average, but seem to sit high on her chest. And her legs… oh, her legs!! … they are long, smooth, toned, and muscular. Not body-builder muscular, but clearly strong enough that it's easy to imagine them tightly wrapped around my waist. I never expected to find them there, but it was a common fantasy.

In short, Jenna was one hot chick, and it was such a pleasure seeing her every few weeks. I never openly ogled her, but I couldn't resist occasional glances to her chest or legs when neither she nor my wife was looking. These images were quickly locked in a secret memory compartment in my brain, accessed whenever I was masturbating. I admit that once or twice the images slipped to the front of my consciousness while having sex with my wife. Those always led to the most powerful orgasms, which more than made up for the modicum of guilt I felt.

It never occurred to me that Jenna may have noticed my stealing glances, nor that she might find me attractive as well.

ONE FRIDAY NIGHT

Two weeks ago, on a Friday night, Jenna babysat for us. My wife and I went to dinner and a movie, returning around 10:30 p.m. Jenna happened to mention her plans to go to Foxwoods casino the next day, and that somehow led to a conversation about the best route to get there. I was confident that one route was best, but my wife was certain that a different approach would get them there sooner. Before long, my wife was seated at the computer pulling up Yahoo Maps in a vain attempt to prove herself right.

Jenna and I stood behind her, side-by-side, as my wife clicked away on the keyboard. Jenna's hand rested on my back as she leaned over slightly to see the computer screen. I felt Jenna's hand caress up and down my back – over my shirt – as we both watched the computer screen and continued debating the best driving directions. Although this was unusual, it was not necessarily inappropriate or threatening, so I didn't acknowledge it and just enjoyed the feeling of her hand lightly exploring my back.

As the map and directions appeared on the screen, Jenna and I both leaned in closer. As we did so, Jenna's hand traveled down my back to the bottom of my untucked shirt, and then I felt her fingers slip underneath to touch my bare lower back. Okay, this was probably inappropriate, but I wasn't sure what to make of it. I looked over at her in surprise, but Jenna was not paying attention to me. Her eyes were fixed on the computer screen, and she was commenting on the directions that appeared there. But her hand and fingers moved higher beneath my shirt, her fingernails lightly scraping up and around my back.

Her touch made my whole body shiver, but my wife, still sitting in front of us, did not notice. However, I could tell my reaction brought a smile to Jenna's face, and seemed to embolden her. Her hand and fingers continued their exploration of my back, alternating between her palm, fingertips, and finger nails. It felt absolutely wonderful, not to mention erotic as hell. My wife was about to give up, conceding that my driving recommendation might be better after all, when Jenna suggested she try another website just to make sure. Jumping at the chance to salvage her pride, my wife continued to tap away at the computer.

The extra time allowed Jenna to continue rubbing and tickling my back beneath my shirt. At the same time, she leaned into me so that our sides and hips were pressing up against each other. That gave her enough room to reach around me further, so that her fingers could wrap around my side and just barely reach my sensitive nipple. She flicked her finger tips and finger nails across my right nipple, all the while looking directly at the screen and maintaining a steady flow of mindless chatter. My cock was rock-hard by this time, but I managed to stay quiet, trying desperately to control the impulse to flinch and groan as she played with my nipple beneath my shirt, squeezing and pinching it relentlessly.

Time hovered until the second website reconfirmed my directions and my wife slid the chair back to get up. Jenna and I stood upright to give her room, and Jenna removed her hand from beneath my shirt, rested it on my buttocks just long enough to give them a squeeze, and then separated herself.

She looked at me and smiled broadly. Thanking us both for the directions, she said goodbye and headed out to her car. She carried her smile with her out of the house, while I hid my raging hard-on from my wife.

YESTERDAY EVENING

The next time Jenna came over to baby-sit was just last night. When I opened the door, I was immediately struck by her outfit, which seemed more revealing than is typical for her. She wore a low-cut T-shirt, very short shorts, and flip flops. My eyes involuntarily traveled down her gorgeous legs as I burned the image into my memory for future use. Man, is she hot!

I welcomed Jenna into the house. "Sarah is still upstairs getting ready, with the kids, so it'll be a few minutes," I explained as I reclaimed my seat in the large easy chair in the family room. "Make yourself comfortable." I picked up the magazine and flipped to the article I had been reading. Jenna stood nearby, looking across the room towards the stairs and listening.

"How was Foxwoods?" I asked.

"Oh, it was just okay," she answered. "I think it would have been more fun if there weren't so many people smoking all over the place."

I nodded in agreement. "Did you gamble? Make any money?"

"I played slots for a little while, but not too long. A bunch of guys were hanging around me, making stupid comments and coming on to me. Made it pretty hard to enjoy the game." I didn't know how to respond to that, so I just grunted and turned my attention back to the magazine.

Jenna stepped in front of me, slipped her right foot out of her flip flip, and placed her bare foot on the chair cushion, right between my legs. "Do you think I have nice legs?" she asked in an innocent tone.

I immediately sat bolt upright, quickly placing the magazine down on the armrest. My expression must have registered my surprise and discomfort, but it did nothing to dissuade Jenna from her seductive behavior. Did she even know how forward she was, or was it really just an innocent, well-intentioned question?

That question was answered right away. "So, what do you think? Do I have nice legs?" As she spoke, Jenna slid her foot forward until her toes lightly grazed the crotch of my cotton pants, and she glanced back over toward the stairs.

"Uhhhhh. Yes, Jenna, your legs are beautiful." I responded truthfully, trying to push myself deeper into the chair to keep distance between her foot any my growing erection.

"I think a lot of guys like my legs. People seem to stare at them all the time. Sort of like you do sometimes, Andy." She pushed her foot forward slightly and wiggled her toes. I could definitely feel the movement against my covered prick, and my hands shot out to grab her calf and push her leg away.

"Jenna, what are you doing?! We can't—"

"What's the matter? Am I making you uncomfortable?" Her eyes shone brightly and her face broke into a broad smile. Without warning, she tightened her leg muscles and pushed forward against my unconvincing resistance, pressing the ball of her foot firmly against my dick. I groaned deeply and threw my head back, eyes tightly shut.

She rotated her foot around so that it was rubbing all over my shaft, alternating between the ball of her foot and her toes. I still gripped her calf, but now leaned forward a bit and pulled her leg closer to me, enjoying the feel of her firm muscles beneath my fingers, and lifting my hips to meet her foot. It felt absolutely incredible!! Push, wiggle, rub, rub, rub, rub, rub. I rocked forward to increase the pressure, and she picked up the pace. My arms now hugged her leg, my cheek rested against her knee. Rub rub rub rub rub. I moaned and groaned as bolts of pleasure shot through me.

And then we both heard my wife and kids coming down the stairs. Jenna rubbed just a few moments longer, and then quickly pulled her foot away, returned it to the flip-flop, and stepped away. I whipped the magazine in front of me, covering my engorged, throbbing dick.

When I had recovered enough, I got up and my wife and I left the house. What a night!

LAST NIGHT

It was hard to concentrate on anything that night. Jenna, whom I've known for years as a sweet, young, innocent (and admittedly gorgeous) kid was making serious moves on me. While the little head in my pants was eager to plunge into her dripping pussy while her legs tightly gripped me, the more rationale head on my shoulders wanted to keep a safe distance between us. I've got a good marriage, and I didn't want to fuck it up.

So it was with mixed feelings that I wondered what fate had in store for me as I pulled the car into the garage and shut off the engine. Sarah and I went inside the house and found Jenna stretched out comfortably on the sofa watching TV. She confirmed that the evening had gone smoothly and the kids were asleep.

I handed Jenna some money with a quick "thanks" and then abruptly went upstairs, leaving my wife to say goodbye and lock up the house. Phew. Escaped that one.

A few minutes later, my wife called upstairs to me. "Honey, can you please drive Jenna home? Her car won't start." Pause. Heart palpitations. Sweat. Gulp. "Honey? Did you hear me?" Uh oh. I went back downstairs, trying to figure out how to handle this turn of events. But there was no way out, since I knew my wife really didn't want to go herself.

Jenna was across the room, talking hurriedly but softly into her cell phone. She snapped it closed, apologized for the inconvenience, and thanked me in advance for my help.

"Thanks, honey," sighed my wife as Jenna and I headed out the door. I glanced over at Jenna, who was smiling coyly to herself.

We climbed into my car, backed out of the garage and down the driveway, and hit the road. Jenna looked cute as hell sitting there in the passenger's seat, seatbelt pressing between he breasts and shorts only barely covering her smooth legs.

We didn't talk at first. Then Jenna looked over at me and said, "Did you have a nice time tonight?"

"Yes, thank you. We went out with friends we haven't seen in a long time, so it was fun to catch up." I kept driving, my eyes fixed on the road.

"Did you have fun earlier too, before you went out?" she asked, scooting a little closer to me.

I paused. "Jenna—"

"It's just that you seemed to really enjoy it," she interrupted, sliding her left hand over to rest against the side of my leg.

I gulped, but kept my eyes on the road. "Jenna," I continued, "we really can't—"

She slid her hand up on my thigh, used her right hand to unbuckle her seatbelt, and scurried across the seat so that she was pressed up against me.

I flinched, swallowed hard, and opened my mouth to speak again, but didn't get the chance.

"Shhhhhhh… I just want to feel it again, just while we're driving." Jenna squeezed my thigh with her left hand, and reached her right hand across and placed it on my crotch. She traced her fingers up and down, finding my dick's position beneath my pants, and then cupped her fingers around its expanding width and squeezed. I shuttered and moaned quietly as she manipulated me. She alternately rubbed and squeezed on top of my pants, while resting her head against my shoulder.

We were about half way there, and Jenna picked up the pace a bit, rubbing faster and with greater pressure, and using her left hand – still on my thigh – to pull my leg toward her slightly.

I concentrated on staying on the road, occasionally grunting in guilty pleasure. Jenna concentrated on tormenting me as much as possible. "You just keep driving," she said as her hands moved up to my belt and opened it. I moaned loader, but said nothing. Drive drive drive. She unbuttoned my pants, and then slowly pulled down the zipper. She then spread open the flaps of my pants and placed her hand back on my rigid dick, on top of just my underpants now. Her rubbing and squeezing continued. At the same time, she moved her other hand down the inside of my bare thigh and slipped her fingers beneath the leg band of my briefs, where she found and tickled my scrotum and balls.

I was beside myself with excitement. Her seduction was bringing me close to orgasm, but I was not yet entirely relieved of my senses. Summoning up all my inner strength, and emboldened by our arrival to her dorm building, I pulled her hands away and breathlessly told her we couldn't go any further. I zipped and rebuckled my pants, but my rigid cock and involuntary body twitches made it clear to Jenna that I was deeply conflicted.

"Oh, but I need you to come inside for a minute," Jenna insisted. Hah! I wasn't about to fall for that one! She saw the look of determined skepticism on my face, put her hands on her hips, and explained mockingly, "Not forthat, Andy. I just need you to fix something. It should be quick." I looked at her suspiciously, but she seemed genuine enough. I nodded and we went inside.

Jenna opened the door to her dorm room, and I immediately noticed a young, dark-haired, bespectacled beauty lying on the bed on her stomach, swinging her feet in the air as she read a book. "Oh, Hi, Trish," Jenna said as we walked in. "Andy, this is my roommate, Trish. Trish, Andy." Trish smiled broadly and gave me a perky "Hi!" as she lay her book down on the bed and lifted herself off the bed.

I glanced around the room. Fairly large for a dorm room, but I knew this was an old building that had been refurbished. It had some unusual features, including a high ceiling, two tall windows, and a support column near the door.

Trish moved towards me, her right hand extended. Gee, I didn't expect any formality, but I stepped towards her and extended my hand as well. Jenna moved with me, along my left side. I reached Trish and our hands came together in a friendly shake just next to the support column. That's when they out-maneuvered me. With great precision and deftness, Trish pulled my hand behind the support column while Jenna suddenly grabbed my left hand and pulled it back as well, forcing me to stumble a few steps and to the side. In the same motion, Trish then snapped the handcuffs (which I now know she had been hiding in her left hand) onto both my wrists. I found myself standing, facing Trish's bed, with both hands locked behind my back around the column. How many times had they practiced this move??!!

The girls jumped up-and-down in triumph, laughing and high-fiving each other.

"Very funny, ladies!" I said in my most authoritative tone. "Come on, let me out of here."

The girls stopped celebrating and surmised me carefully. Trish then walked up so that she was standing directly in front of me. She reached to the top of my shirt and began to unbutton it. "Sorry, Andy. I'm afraid you can't leave until Jenna has some fun with you. You see, she's been talking about you all year, and I'm afraid there's only one way I can get her to shut up about you." Her fingers expertly unfastened the buttons down my shirt. When she reached the last one, she forcefully spread the sides apart and over my shoulders, revealing my chest and stomach. She looked my in the eyes and moved her fingernails up and down my chest, over my nipples and around my sides.

"We've been planning this all week, you know." Her fingers continued to dance over me, and I twitched and shuddered involuntarily. Trish never took her eyes off me. She just kept tickling and rubbing me. "Don't worry, Andy. I think you'll have a little bit of fun too."

It's then that I noticed Jenna had changed into a light cotton bathrobe and had moved in front of me, beside Trish. She reached up, and I had four hands roaming over me. Pinching my nipples. Tickling my sides. Squeezing my chest muscles. "I think he's ready for you," Trish said. She leaned into me and wrapped her lips around my right nipple, sucking it strongly, while four hands continued to dance over me.

I strained against the handcuffs, arched my back, and moaned as they assaulted me. Trish released her oral grip on my nipple and moved behind me. She reached around and continuing to rub, tickle, and pinch me. Jenna looked up at me, her smile stretching from ear to ear, and moved in to take Trish's spot. She kissed and licked me, tongue twirling, while her hands gradually made their way lower. After crossing my lower stomach, Jenna's fingers reached my belt and quickly unfastened it. Trish's hands came down to help as well, and in a matter of moments, my pants and underpants were being pushed all the way down to the floor, my cock springing forward into the open air.

Jenna kissed her way down my front, following the path of her hands, until she reached my throbbing dick. She grabbed it roughly at the base and simultaneously sank her mouth over it. I groaned deeply and arched my back against the column while her wet lips and tight grip started to work me. In and out, in and out, in and out. Trish, still standing behind me, had moved her hands back up to my chest and returned to pinching my nipples. I groaned even louder, and started to buck my hips forward to meet Jenna's rhythm. I could feel a powerful orgasm welling up, and I was well beyond the point of trying to stop the girls.

But Jenna could sense that I was close. With a loud smacking noise, she released my dick entirely and stood up to face me. Her hands loosened the strap around her waist and her robe fell open, revealing her breasts, tight abdomen, and shaved pussy to my disbelieving gaze. She pressed her body against me and kissed me tenderly on the neck. I could feel her hard nipples and warm thighs against me. She moved her hands to my shoulders and pushed me down.

Willingly, I allowed my knees to bend so that I slid down the column. When my lips reached her breasts, I paused my descent and eagerly took her nipple into my mouth. Jenna gasped and purred, wrapped her hands around my head, and pushed my face into her breasts. My tongue danced over her nipple as I sucked and lightly nibbled. Jenna's moans increased, but she moved her hands back to my shoulders and continued pushing me lower. I sank all the way down to the floor, stretching my legs out in front of me. Jenna straddled me and moved her hips towards my face. I gave her pussy the same treatment that her nipple had enjoyed. I couldn't believe how wet she was, but her musky odor only inflamed my passions more. I licked and sucked, darting my tongue into her folds and around her swollen button. Again, Jenna grabbed my head and pushed my face into her, rolling and bucking her hips to maximize her pleasure, and moaning uncontrollably.