As a happily married man in my mid thirties, I never expected or desired for the following to take place, but it did.
One Friday night in the fall my wife was gone and my two young daughters had been babysat while I went to a sporting event. I returned home late that night and the kids were fast asleep in their beds. Cara had watched my kids along with her young one as well. She was 19, thin build, shoulder length dirty blonde hair and brown eyes.
As I entered the living room and said hello, Cara told me, “My son is asleep in your bed. Do you mind if I wait a few minutes before moving him to the car?”
I softly responded, “No, not at all,” and sat in my recliner.
She told me how the night went with the kids and I gave her the agreed upon fee for watching my kids. We made a little small talk and she mentioned her son’s father derogatorily and went on to say, “I am in no hurry to, nor have any desire to, date.”
I nodded and said, “That is understandable.”
Cara said, “If I get horny I have my fingers or a dildo.” I laughed awkwardly and nodded.
I said, “It’s not the same I hear, but I get it.”
Cara responded, “Not like I really know much. His dad and I slept together a few times and I really don’t know if he was good or I was good or what the fuck ever. Nothing but missionary position since we were inexperienced.”
I smiled and said, “You poor thing; missionary is so boring and you can have so much more fun than that with sex.”
She questioned, “Do you mean foreplay? He played with my boobs, not like there is really much there to play with.”
“Yes, foreplay is one thing but more to it than playing with boobs. Also, way more enjoyable positions than missionary,” I replied.
“Well, I wouldn’t know about any of that. I don’t have time for a guy with my son and work and living at my parent’s house. Plus, any of that scares guys away or makes it impossible even if I wanted it,” she said.
“Maybe you need a guy who can just be your fuck buddy. That can be your booty call when you have time and want it,” I responded.
She replied, “That could work if he was a man and not a boy and had his own place and shit. If he would understand on my timing too and no relationship just satisfying my needs.”
I said, “Well, you have an idea now you just need to find the guy to fit that for you. You are an attractive girl, so you shouldn’t have a problem finding a guy attracted to you. Just laying down your guidelines may be the challenge.”
Cara smiled at me and said, “Yeah, the guidelines will be hard cause some guys are stupid. But if the guy would be patient and understanding, I would let him teach me things. I have seen some porn and some stuff interests me to try.”
I smiled and said, “Maybe a guy will be more willing to abide with your guidelines when you explain that to him.”
Cara looked at me and said, “Would you be up for teaching me stuff? I know you’re married and I don’t want to fuck with that, but you like, understand my circumstances, and you said I was attractive.”
I was thrown off by her question and paused for a few seconds before responding with, “Yes, I am married and have a family and will not jeopardize that. I can help you find someone if you want.”
Cara slumped into the chair and said, “I’m sorry I asked.”
“Don’t apologize; I am honored you asked me. No harm done.”
She looked at me and asked, “If you weren’t married, would have you agreed to help me?”
“In a heart beat I would.” I answered.
Cara said, “I promise to never tell anyone or get attached or jealous or anything. We could like email or whatever to not jeopardize you getting caught.”
“Well, if we can ensure we don’t get caught, and agree this is a short time thing, and agree to a set of rules and guidelines, then I guess we can give it a shot.”
Cara smiled and said, “Oh thank you, thank you. Ya whatever you want. Thank you.”
We spent 15 minutes writing an agreement and signing it. The agreement outlined the arrangement, rules, and she agreed to do whatever I asked with no disagreement or questions.
Once it was signed she looked at me and questioned, “When and what is lesson number 1?”
I smiled and said, “Well, I want to want you bad, so strip down to your bra and panties.”
Cara smiled and nodded and proceeded to take off her shirt and pants. She stood in front of me in her purple laced thong and beige bra. I instructed her to turn around so I could observe and take in all of her. Her boobs were an A, maybe B at most, but she had a tiny cute little butt.
She joked, “I told you I have no boobs.”
I remarked, “You have enough there and plus you make up for it with a sexy ass.”
She smiled and playfully slapped her butt with one hand. I reached for her hips and pulled her to me and softly kissed her stomach before slowly pulling down her thong. Cara shuddered for a second as I looked at her smooth pussy.
“Damn, you have a pretty pussy!” She smiled and I gently kissed her pussy lips. I said, “Now I am going to show you what it’s like to get your sexy pussy eaten.”
She laid down on the couch and I opened her thighs with my hands and slowly licked her pussy lips and into her pussy my tongue went. Cara began to moan as I ran my tongue back and forth inside her. Her pussy was soft and had a sweet taste to it. She moaned more and more and I felt her pussy twitch as she orgasmed and a rush of her sweet juices filled my mouth. I kept pleasuring her pussy with my tongue and she orgasmed more and more till she had one huge orgasm and I finally stopped.
Cara remained on the couch sighing and said, “Shit, that was fucking incredible! Definitely need that again soon.”
I laughed and said, “In time.”
Then we heard her cell phone go off and she reached for and looked at it. She said, “Shit, it’s my mom wondering when I will be home. Guess I better go so she doesn’t get suspicious.” She got up and began putting on her underwear, pants, and shirt. I assisted her getting her son in the car.
I said, “It’s a shame you have to end the first night as it was getting good.”
Cara smiled at me and said, “I could put him in his bed and make up some shit of hanging at a friend’s and come back if you want.”
I smiled and said, “Sounds good to me.”
She gave me a hug and said, “I will be back in an hour.”
She shut the car door and drove off. I went in the house and took a shower and trimmed around my cock and balls. As I was getting dressed I got a text from her saying she would be on her way. I text back asking for a pic of her ass and she quickly sent a selfie of her ass. Her next message said leaving now. I put on a tee shirt and some shorts, but I figured why bother even putting on boxers. I watched tv as I waited for her return and after 15-20 minutes I got a text saying she was here. So I put the dogs outside and let her inside.
We went to the living room and immediately my hands gravitated to her ass and I cupped a cheek in each hand as I hugged her. Then I said, “How would you like to learn about sucking cock?”
She smiled and said, “I’m down for that. Never done it before but I saw it done on porn and will need some guidance too.”
I said, “Well you can do what you have seen on porn and I will guide you, too.” Then I lifted at the bottom of her shirt and said, “First, this shit needs to go.”
She took off her shirt and bra too when I pointed at it. I glanced at her small tits and began running my tongue around her nipple before taking all of her boob in my mouth and sucking on it. Back and forth I switched sucking on her boobs one at a time in my mouth for 10 minutes while she sat on my lap. I felt my cock starting to slightly stiffen and I placed her hand on my crotch and she took the hint and began stroking my cock through and eventually inside my shorts.
I smiled and her and said, “Time to use your mouth.”
She climbed off my lap and knelt on the floor and pulled off my shorts. Cara wrapped one hand around my shaft and stroked it and slowly took the head to her lips.
I said, “Cup my balls and stroke them with your other hand.” She took the instruction and did so and then she opened her lips around my cock and began taking me in her mouth. Cara softly sucked up and down the shaft and rubbed my balls. “Yes, that’s it. Good job!” I complimented. As I complimented and encouraged she took more of my cock in her mouth till she was just about to my balls.
“Very fucking nice and you said you never did this shit before. I never would have known.” She looked up at me with a smile in her eyes. I said, “Go down the shaft and suck on my balls.” Cara followed instruction again and took my balls in her mouth and sucked. After a few minutes of ball sucking I instructed her back to my cock for a few more minutes before tapping her on the shoulders to stop and saying, “Alright, time for pleasing you again.”
As she stood up I questioned, “Did you enjoy sucking cock?” Cara nodded her head and opened her mouth to answer and I saw a mixture of saliva and pre-cum on her lips and tongue.
“Yes, it was fun!” she said.
I instructed her to pull off her shorts and panties and she did and then I kissed around her pussy and her ass as she stood in front of me. Slowly I ran a finger around her pussy and inside her and softly began fingering her. It didn’t take long for her to begin moaning and her knees went weak and she almost fell on me. I caught her and I guided her to and instructed her to bend over the edge of the couch and spread her legs. I licked inside her pussy for a few minutes and she became very wet.
I asked, “Are you ready to get fucked in my favorite position, doggy style?”
She nodded and moaned a yes. I slowly guided my cock into her tight wet pussy and grabbed onto her hips. I began pumping slow at first and getting harder and harder. Cara moaned louder and louder and I asked, “Do you like it? How’s your pussy like this?”
She softly answered, “I fucking like it!”
Her tiny ass slammed against my hips and I said, “Your sweet pussy feels so good and your ass is fucking beautiful.”
She moaned louder and I felt her pussy contracting and she buried her head into the couch to muffle a scream of ecstasy. I continued to pound her harder and harder until I felt myself getting close and I said, “Get ready!” With two more hard thrusts I exploded a load in her pussy. She laid bent over the couch as I walked to the bathroom and cleaned myself off.
I came back and said, “So, do you like doggy style more than missionary?”
Cara answered, “Fuck yeah, I do! I never felt shit with missionary like I did that time.”
I said, “Yeah, doggy gets in deeper and hits the right spots. Plus you were fucked by a man, not a boy.”
She smiled and said, “That is a difference.”
Then I heard one of my kids whimpering so I went and comforted them for a couple minutes before returning to the living room where she was dressed.
She said, “I’ll probably call it a night for my son’s sake and your kids and such.”
I said, “If you must. My kids are staying at a grandparent’s house tomorrow night, would you be able to have your son watched for the night by your parents and we can have more lessons?”
Cara smiled and said, “I can ask my mom in the morning, but it shouldn’t be an issue.”
“Wonderful. I will text you some instructions tomorrow once you confirm,” I said.
She smiled and nodded in agreement before kissing my cheek. I slapped her ass as she walked out the door. I closed the door behind her and shut off the porch light as I saw her car lights back out of the driveway.