I used to let our babysitter Sherry watch my wife Jeannie and I together. When she was barely 18 and very curious and untouched by any guys yet, because their family lived out in the country, away from everyone. Sherry was always asking me teasing questions about sex.
"Does Jeannie ever suck you?"
Shocked, I smiled and said, "Sometimes. Why, would you like to watch her suck me?"
"Sure!" she said.
So one Saturday morning, I was feeling horny, just thinking about Sherry's sweet looking ass. She would be coming up the road shortly, as she would spend the day with us and watch our kids that night.
I met her at the gate, before Jeannie saw her. I told Sherry to go out to the tool shed, beside the cornfield. I took my Jeannie outside, between two rows of corn. I turned sideways, to allow Sherry a good view out the window of the shed. As my wife dropped to her knees, I took my cock out and stroked it a few times, just to show off its size. After letting Sherry watch Jeannie suck my stiff cock for a few minutes, I told my wife to turn around on her hands and knees. I yanked her shorts down, taking my cock in my hand. I looked into Sherry's eyes, as I began rubbing my cock up and down my wife's slit. Sherry's eyes widened as I began pumping Jeannie's pussy. I held her hips and began giving her long, deep strokes. Never taking my eyes away from our young babysitter's peeking eyes, I drove my 9" cock into my wife's juicy, inviting cunt. I glared into Sherry's eyes, as my body began jerking and my balls pumped hot thick wads of cum, deep into my wife's snatch. The fact of being watched by her caused the fuck session to end way too fast.
Later that afternoon as Jeannie was starting the fried chicken for supper, I told her I was going into town for beer and soda.
Sherry heard me and excitedly asked, "Can I ride along? I never get to go anywhere."
Jeannie looked at me and nodded her approval. I replied, "Sure, let's get going. I want to be back for the ball game at 4:30."
I knew that this would be an interesting 22 mile ride to town and back. I watched her walk to the van, clad in terry cloth shorts and sandals. Her thin, worn, short T-shirt allowed her flat young stomach to show. As she climbed into the van, I could see she was bra-less, as the bottom halves of her firm round breasts were visible. My cock gave a twitch and I tried to push the sight of her young breasts out of my mind.
The first couple miles of the ride were quiet. Then Sherry broke the silence with, "Thanks Jim."
I asked, "For what, letting you ride along?"
She smiled at me and said, "No, for letting me watch you and Jeannie together. It was really exciting. I've only seen one cock before and I loved how yours looked when it got long and stiff. The other cock I've seen was my dad's best friend Henry. He caught me sunbathing nude behind our barn. He asked me if my parents knew I laid around naked outside? I told him no and please don't tell them. He said it would be our little secret and he smiled. Then he told me to get up on my knees and come to him. I wasn't sure what he wanted, until he started unzipping his jeans. His cock was hard and he had trouble taking it out. Then he moved close to my face and told me to take his cock in my mouth and suck on it. When I resisted, he said, ‘You don't want your parents to find out about your nudity, do you?’ So I had no choice, except to do as he said. I sucked him for about five minutes and then he jacked off on my breasts."
"OK, that's enough talk for now. I don't want to walk into the store with a hard-on tenting in my jeans." It was quiet for a mile or so and she spoke up again.
"Watching you two gave me a strange reaction. When you guys were done, I noticed my panties were wet."
I replied, "Yea right."
She got out of her captain's chair and crawled over on her knees beside me. "Feel them. They're still wet," she said.
"Please, I want you to feel them," she begged.
I placed my hand on the small of her back and easily slipped it into her loose-fitting shorts. I traced her ass on the outside of her panties. Slowly sliding down, I allowed two of my fingers to glide between her upper thighs and gently rest on her moist, puffy pussy lips. "Mmmm," she purred. "That feels so nice. Play with it Jim. Please?"
My heart was racing and my brain waves were all in my hardening cock. We were nearing the store, so I pulled my hand out of her shorts to allow for steering into the parking lot.
"Don't stop yet?" she whispered.
I drove around behind store and parked away from the building. Still kneeling, Sherry spread her knees a little further apart. Leaning forward more, she laid her hands on my lap. Gently she began rubbing my erection, through my jeans. I slid my right hand back into her shorts and traveled back to her wet, waiting cunt lips. As I began teasing her slit back and forth, she reached for my belt and undid it. She took hold of my zipper and asked, "May I?"
There was no stopping now. "Please do," I answered.
As she slowly unzipped my jeans, I pulled her panties aside and slid my finger inside them. As I began tracing her slit gently up and down, she fumbled around freeing my hard cock from my boxers.
She wrapped her hand around my cock, started sliding it up and down the length of it. She let out a soft moan, as I began easing my finger into her wet, waiting, virgin hole. As I started fingering her deeper and a little faster, she stroked my cock faster.
Stopping for a moment, she asked, "What now?"
I whispered, "Do what Jeannie did to it in the cornfield this morning. You watched how she did it, didn't you?" As I started pushing my finger deeper into her juicy cunt, she leaned down and started kissing the tip of my cock.
As I started finger-fucking her, her kisses turned to licks. I whispered, "Take my big dick into your mouth Sherry and suck it."
She asked, "Tell me how to suck it?"
I told her, "Go slowly down on it and suck softly on the way back up."
Instantly, I knew she was a natural at sucking cock. I knew I wouldn't last long, so I started really jacking her off. I knew that if I brought her to her first ever orgasm, she was mine anytime I wanted her. Reaching under her T-shirt with my free hand, I rolled her nipple gently between my thumb and finger. What sweet young firm titties, I thought.
The moment of truth arrived! As she took my long hard cock deeper, I feared gagging her? I feverishly continued to finger-fuck her tight young twat. Her body began shaking and her pussy muscles tightened even more on my finger. "Ohhhhhhhh," she moaned, as her bucked like a bronco. That's all it took! I started to empty my balls, pumping cum deep into her throat. Never choking once, she sucked me dry. When I finished, she continued to suck it clean.
"We'd better shop and hurry home," I said.
That was some great head! I knew I wasn't done with her yet. On the way home, I told her to play sick Sunday and let her parents go to church alone. “I'll come see you, because I have something for you.”