Literotica, Sex with Strangers

Literotica: Chaperone

I’m a stay-at-home dad working out of my home as a cartoonist and my wife works as a corporate attorney. Her job pressures have put her working more and more hours leaving little time for the two of us.

I spend a lot of time with Jeremy, my third grade son and have gotten involved with class outings and projects. Sonya Shell is his teacher and I was drawn to her infectious smile and perky personality ever since parent’s night last fall. She’s a petite little thing, about 5’4″ and probably 100 pound soaking wet. She usually wears blouse with a skirt and at least 2-3″ heels to make her seem taller. Her toned, slender legs as she walked was enough to make me drool and the way her “B” cup breasts bounced could bring a woody in seconds.

I let her know early on that I was available for chaperoning field trips and stuff, since I’m always home. She is a real bubbly thing with a syrupy southern drawl and loves to touch you on the shoulder or arm when she talks. Needless to say, with the limited attention I was getting at home, I really enjoyed Sonya’s attention. Maybe I was reading more into it than I should have, but she seemed to hold her gaze on me a little longer than with the other parents and my wife Jill was never around to care.

One afternoon towards the end of the school year, Sonya called me for a favor. “Jack, would you be available to go along on the year-end class party to the water park next Thursday?” she sweetly asked. “Sure Sonya, I’d love to” I quickly replied, almost a little too quickly. “Great, just be here at the school at 9:30 and we’ll go from there, and don’t forget your swimsuit!” she added.

I suddenly had visions of Sonya strutting around the water park in a bikini and I could feel my cock starting to stir. “I will if you will!” I answered. She giggled a little on the other end of the line and said “Then it’s a date!” As I hung up the phone, I started to paint a mental picture of her firm, slender body, dripping wet from a water slide and watching her nipples protruding from her bathing suit.

I didn’t even bother to tell Jill about the water park trip. The sun was out early and the temperature already about 75 when I arrived at the school in my “62” Cadillac convertible. I was wearing khaki shorts and a 3-button polo shirt. As I pulled up to the school parking lot, I saw Sonya in a pair of very short, white shorts and a denim top that she had tied the tails at her waist exposing her flat tummy.

She was herding the kids into the bus and waived to me as I approached. “Hi Jack! Great day huh?” “Looks like you picked a great day for the water park!” I said as I tried to nonchalantly eyeball her magnificent legs and ass. Sonya turned to me with a quizzical look and asked “Would it be too much trouble for you to drive your car?” “It looks like we’re a couple seats short in the bus.” “Sure, it’s no problem.”

I started to wander back towards my car when I heard the bus start up and the doors squeak closed. I turned to see Sonya walking briskly toward me as the bus started to pull away from the curb. I was immediately shouting inside my head “All right, alone with her for the whole trip!” I opened the door for her as she slid into the big leather bench seat and threw her bag into the back seat. I unhooked the latches for the top and retracted the convertible top. “This is a great car Jack… This is going to be great!” I thought so too as I slid into the car and took a quick glance at her shapely legs curled sideways underneath her.

We followed the bus out onto the street and headed towards the freeway. Sonya was sitting on her feet and turned towards me as we talked. Our conversation quickly turned to relationships. She asked, “How come I’ve never met your wife?” I kind of rolled my eyes and said, “Jill has a very demanding job and it requires a lot of her time, sometimes 60 or 70 hours a week.” Sonya replied “Must be kind of hard on you, huh?” I glanced at Sonya and just shrugged my shoulders.

“What about you, got any guys on the hook? I asked. “Naw, not really. Most the guys my age are more concerned about career than romance.” I shook my head in disbelief “With you looks and brains, I’d think guys would be tripping over themselves to get close to you!” Sonya lowered her head and remarked “Guys think my boobs are to small.” I couldn’t believe this conversation was going! Then I even surprised myself when I replied “You have beautiful breasts, I think they’re perfect!”

“Holy Shit!” I thought. Here I am, a married man, following a bus load of kids that included my nine year old son, and I’m telling this 24 year-old teacher that she has nice tits!

“You really like the way they look, Jack?” Sonya asked. I turned to her a took a long gaze as she sat up straight and thrust her chest upward to accentuate her chest. I could feel my cock starting to swell as she thrust her pert breasts toward me. “They’re really magnificent Sonya.” As I turned my eyes back to the road and tried to hide the discomfort of my hard-on growing in my shorts.

We reached the freeway and the bus happened to make the traffic signal ahead of us and we had to stop. That allowed the bus to get well down the freeway before we were able to get on. Sonya then said “I’m sorry Jack, maybe I’ve treaded into forbidden territory talking about this stuff with you.” I looked at her and answered “Sonya, I think it’s great we can talk so freely about things with each other.” I could feel my heart pounding as the words left my mouth. I knew I was opening the door to go further. Sonya slid a little closer to me on the front seat and her hand touched my shoulder “I really like you Jack, but I wouldn’t want to do or say anything that would ruin our relationship”.

I thought to myself “We have a relationship?” Just then, Sonya continued, “I know you find me attractive and I think you’re about the sweetest and sexiest man I’ve ever met.” Her other hand crossed over and settled on my thigh. My cock was coiled up in an uncomfortable knot inside my Jockeys and her hand being so close made it grow even more. “If I’m overstepping my bounds Jack, just say so and I’ll back off.” She said in a low raspy voice. I glanced sideways and could see down her shirt and the swell of her breasts were in plain view over the lacy cups of her white bra.

Up ahead, I could see the bus exiting the freeway to a secondary highway so I knew we were still about 15 minutes away from the water park. As I glanced over again, Sonya had unbuttoned a couple more buttons of her shirt and pulled it apart to allow me a clear view of her tits. “Do you like what you see Jack?” she cooed. I starred without speaking. Sonya’s hand on my thigh started slowly moving up my thigh until she was massaging my hardness through my shorts. “I guess that’s my answer, huh?”

We were on a two lane road now and I slowed way down so the occupants of the bus wouldn’t be able to see what was going on in my car. “Oh Sonya……….” Is all I could utter as she deftly unbuttoned my shorts and slid the zipper open. As if I was having the most erotic dream imaginable, I watched as she lowered her head into my lap. I raised my butt off the seat as she skid the shorts and Jockeys down and my cock sprang to full attention. “Ooooooooooo Jack, it’s wonderful!” she whispered as she looked up from my lap. Her fingers wrapped around it and slowly began pumping my 8″ up and down as her face drew nearer.

I’m sure I was swerving in my lane and I had to really concentrate on driving as I felt Sonya’s mouth descend over my engorged head. “Ohhhhhhhhhhh Gawwd!” I gasped as her mouth closed around my cock shaft and her hand fondled my balls. I began gently pumping my hips up off the seat and fucking her warm, moist mouth. This was a totally awesome experience, especially since my wife never wanted to give me a blowjob in all of our 12 years of marriage. I rested my right hand on Sonya’s back and ran my fingers over her bare back and down to the bottom of her tailbone.

I saw the sign for the water park “2 miles ahead” “Oh, Sonya, we’re almost to the park.” Sonya began sucking hard on my swollen head and flicking her tongue into the slit of my cock. Her hand lowered down and soon she was rubbing her finger around the rim of my ass. My hips were bucking and I was starting to moan constantly. Just as Sonya slipped her first knuckle of her middle finger into my ass, I exploded in her mouth. “Aaaaaaaarrrrrrrrrrghhhhhh” I bellowed as I felt the most powerful climax of my life rock through my body and stream after stream of my cum shot down her throat.

Sonya helped me get my shorts back on and she buttoned up her shirt just as we turned into the parking lot. I purposely parked a few rows away from the bus to have a minute to re-compose myself. As Sonya reached back to grab her bag, I said “That was the most amazing thing that’s ever happened to me.” Sonya opened the door and shut it behind her and looked at me with a smile “Can’t wait until the ride home!”


Leave a Reply

Your email address will not be published.