Courtney had been the babysitter for our neighborhood from the time she was fifteen. She was the dependable babysitter parents relied upon and every kid loved. She was a skinny redhead with green eyes and a shy personality. Although my wife Jan and I had no children of our own, every kid in the neighborhood knew where to find our garage freezer. We kept it stocked with ice cream bars and other frozen treats for them to take whenever they wanted. Courtney included.
As retirement approached, my wife and I decided to downsize and we moved to a smaller home across town. We tried to stay in touch with friends but as time moved on we started losing touch with people.
One day we received an invitation in the mail to a college graduation party from Courtney’s mother Angie. I couldn’t believe it. I still pictured a skinny redhead watching the neighborhood kids. When we looked at the date my wife said that she had planned a weekend getaway with some girlfriends. But she encouraged me to go. I rsvp’d and looked forward to seeing old friends.
On the day of the party my wife was already gone. I cleaned up and lounged around the house until it was time to head to the party for Courtney. When I arrived I was immediately greeted by friends I lost touch with and caught up on news from everyone.
Suddenly I caught sight of a gorgeous redhead talking to a group of young people. She wore an emerald green body suit that looked like it had been spray painted onto her incredible body. She turned and smiled, she broke away from her friends, approached me and gave me tight hug. Without encouragement my penis immediately started swelling in my pants and pressed into this red headed goddess. I simultaneously felt incredible and hoped I wasn’t offending her by spearing her with my cock.
She broke the hug and said, “Hi Mr. James.”
I suddenly realized that this was who the party was for. “Courtney?” was all I could manage to say.
“Yep, it’s me. How have you been? Where’s your wife? Is she here?”
“I’ve been good. Jan had a weekend planned with some girlfriends and couldn’t make it. She sends her regards. Congratulations, I can’t believe you’re done with college.” I handed her the gift I had brought with me. “It’s not much, but I hope you like it.”
“I can’t believe it’s over too, but I’m glad.” We chatted for a few minutes then she hugged me again and whispered in my ear, “Thank you for the gift. You really didn’t need to get me anything.” Then she said, “I felt you getting hard. And I liked it… do you still have your old cell number?”
As my dick expanded against her again I looked around to see if anyone noticed. Luckily everyone was eating, drinking or talking to someone occupying their time and no one seemed to notice our little encounter.
“Yes, it’s the same one. How did you get my number?”
“I’ve had it a long time,” she told me. “Are you free later?”
“Don’t you have plans with your friends?”
She gave me a peck on the cheek and said, “I have plans for you… I want you to lick me.” Then she walked over to greet other guests.
I self-consciously looked again to see if we had put on an exhibition for anyone. Luckily everyone was self-absorbed in what they were doing. I quickly walked to the bathroom and rearranged my stiff dick and then went out and tried to enjoy the rest of the party.
For the rest of the time I was there whenever I caught Courtney’s eye she’d wink and smile at me. Once she licked her lips provocatively and turned away.
After a couple of hours the festivities were winding down and I was saying goodbyes to old friends when Courtney approached me and thanked me for coming. “It’s been really good to see you.” Then she whispered in my ear, “I’ll call you after this party breaks up. We need to catch up.” I was dumbfounded.
I finished my goodbyes and approached Angie, Courtney’s mom, a beauty in her own right. She had been so busy entertaining we hadn’t gotten a chance to talk. She was a single mom who had raised her daughter on her own, so I told her, “Congratulations. You did a great job with Courtney. You should be proud.”
She thanked me for the compliment and gave me a hug. Her hug seemed to linger a bit and, again, my semi-hard dick, with a mind of its own, got harder and pressed into her.
Angie looked down, smiled and said, “Thanks for coming. Courtney always liked you and you were always so nice. We need to stay in touch. You should call me.” She gave me a light kiss, squeezed my hand and walked me to the door. I started to leave when she called me back.
“Did I forget something?” I asked.
“Just this.” Then she pressed a slip of paper into my hand. I didn’t react to what she had done until I walked to my car and looked at the paper in my hand. I discovered it was Angie’s cell number and a series of X’s and O’s.
I could hardly believe a daughter AND mother had come on to me on the same night!
I drove away and tried to figure out what had just happened. While I lived in the neighborhood I had been friendly with Angie. Even though she was sexy and attractive I didn’t come on to her beyond a little flirting. Now I regretted it. We might have had a good time.
I got home and thought about my wife. We didn’t exactly have an open marriage but what we did with our ‘away’ time we generally kept to ourselves. I knew that on several occasions when she was ‘out with the girls’ she had actually been getting her brains fucked out. I didn’t know with whom and I didn’t really about think about it because it had spiced up our sex life and gave me a hall pass that I had used sparingly. When I did use it no questions ever came from Jan and she seemed to work at pleasing me even more than before. If people knew about this arrangement they might be critical, but it worked for us.
The phone rang and I mistakenly thought it would be Courtney. It was Jan.
“Hi honey. How was the party? How’s Courtney and Angie?”
“They’re fine. Everyone said to tell you ‘hi.’ Can’t believe she grew up.”
“What does she look like? Is she as pretty as her mom?”
“Yes, prettier even. But Angie still looks good too.”
“You never knew Angie was hot for you, did you? I actually gave her a green light with you once when we were talking. But she must have thought I was kidding.”
“Really? I kinda wish I had known. I might have checked in on her after we moved.”
Then Jan said something that rocked me.
“You should fuck her. You both might like it.”
We were talking about our private time and activities and I didn’t want to complicate things, so I carefully said, “That would be… interesting.”
“You know you want to. Try this weekend. Do you need her number? I have it.”
“No, I’ve got it. When are you coming home?”
“That depends, when do you want me home?”
It was Saturday night. “Plan on Tuesday. Does that work for you?”
Jan thought for a minute. “I’ll be alone after tonight, so call if I can come home sooner.” I wondered briefly who she was with. “Love you. Oh, and change the sheets.”
“I love you too. Be careful,” I replied.
As I hung up the phone I realized my wife was probably out on one of her escapades. And she had given me explicit permission to sleep with, actually fuck another woman in our bed! I had no problem with that because I already had a plan. Courtney might have only been teasing me. If that was the case I was going after her mom. Even if she showed up, I was STILL going after her mom.
The phone rang and I answered it thinking Jan had forgotten something. It was Courtney.
By mistake I said, “Hi honey.”
“Hi honey,” said Courtney.
I realized it wasn’t my wife on the line and awkwardly said, “I thought you were my wife.”
Courtney replied, “No it’s just me. Are you free tonight? I really need to see you.”
“I’m not free. Do you think you can afford me?”
“What will it cost?” By now we were dancing to a flirtatious melody.
“Come to my house and we’ll figure it out. But don’t come if you’re just planning to tease me.”
Courtney replied, “Are you sure you want me to come to your house?”
“Yes come to the house.”
“Are you sure? I’m going to tease you AND fuck you and we might make a mess.”
“I hope we do. But I’ve got to ask why you’re not out with your friends or some boy that would die to get next to you?”
Courtney was quiet for a minute and then said, “I’ve thought about you since I was sixteen.”
I was dumbstruck and asked, “Why?”
“I used to listen to my mom and the neighbor ladies talking about you. I got older and I promised myself I’d sleep with you if I had the chance. Many young teenage nights I lay in bed thinking of you, not really knowing why I was wet thinking of you. When I learned to pleasure myself it always started with you. You better be ready for this horny twenty-two year old because I’m going to try and use you up. When you’re fucking your wife you’ll be wishing for me.”
Then I used the most bullshit line in the world when I said, “I was born ready.” We were both silent for a few seconds before we busted out laughing.
I gave her my address and she said, “I’ll be there in an hour. And you better be ready to eat my pussy.”
“My, my young lady. Such language. I may have to spank you.”
“Promises, promises,” she said and then hung up.
Exactly one hour later my doorbell rang. I answered the door and Courtney was standing there. She looked exactly as she had at her party in the same green outfit.
Without a word she was in my arms and our tongues were fighting for superiority. The outline of her body against me felt so good I could have cum on the spot. I could feel every bit of her through her body suit. And I could especially feel her hands groping my cock through my jeans.
As I continued to kiss Courtney I marveled at her firm, athletic body as I started to undress her.
Courtney asked, “I want to do something if you don’t mind.”
“Anything you want.”
“I want you to fuck me in the bed where you sleep with your wife!”
I had planned to do that anyway, so I untangled myself from her arms and led her by the hand to our bedroom. As we walked into my master bedroom, Courtney asked “Where does your wife keep her lingerie?”
Never expecting this question in a thousand years, I asked, “Why?”
“Because I’m going to find something sexy to wear that belongs to your wife while we’re making love in your bed.”
I didn’t know her thinking, but this struck me as the most erotic thing I could think of. I pointed to my wife’s lingerie drawer and said, “Find something. Hurry!”
I took the rest of my clothes off, pulled back the sheets on the bed I shared with Jan and climbed in. As I watched Courtney rummage through the lingerie drawer she picked out a pair of crotchless black, lacy panties and a matching lacy bra that my wife had just bought. She turned and slipped off her green outfit and dressed in my wife’s lingerie.
“What size shoe does your wife wear?”
“I don’t know, six?”
“Perfect. That’s my size.”
Courtney stepped into my wife’s walk-in closet and I could hear her looking through Jan’s shoes until I heard her say, “Perfect.”
As I laid in bed stroking my hard on, Courtney stepped into view. She looked stunning.
Her red hair spilled down framing her beautiful face, the sexy bra barely concealing her 34DD breasts.
Her flat stomach and toned legs were perfectly set off by my wife’s 4 inch stiletto heels.
“You like?”
“Yes.”
“Do you remember I told you I told you I wanted you to lick me?”
“Yes.”
“Good.”
She walked to the bed and leaned down and kissed the head of my cock. She looked up and said, “Switch places with me.”
She lay on the bed as I stood up. She smiled at me and spread open her legs revealing a neatly trimmed pussy.
“I want you to eat me and lick my pussy, please.”
I needed no more prompting and lay down on top of her. I kissed her open mouth, then kissed my way down her incredible body.
Her neck was freckled and as I gently kissed her neck Courtney asked, “Don’t leave any marks where people can see them, okay?”
As I slid down her body I stopped at her perfect tits. Her skin was so pale here that I could see the blue veins running underneath. Her nipples were hard, pink and looked like a school child’s eraser. I had always thought of leaving a ‘hickey’ on a woman’s breast, and now I was going to do it. I sucked on one nipple and then switched to the other as Courtney squirmed beneath me and moaned. After a few minutes of sucking her nipples, I moved to her underboob and sucked with as much force as I could without stopping for a minute.
“Oh fuck! What are you doing? That feels amazing!”
“I’m marking you so you remember tonight.”
I looked at my handiwork and saw a purple welt under her right breast. It was the size of a half-dollar and stood out against her pale skin.
“What do you think?” I asked her.
“I’ve never had a ‘hickey’ before, but it felt amazing while you were marking me.”
“I’m not done,” I said and moved down her body and kissed her flat stomach before arriving at her neatly trimmed bush. The hair on her private area was as red as the top of her head. I kissed the lips of her labia like I was kissing her mouth and pushed my tongue into her dripping cunt, tasting and exploring at the same time. I lifted her legs and kept licking her until I reached her asshole. I licked back to her pussy and found her clit and started gently sucking. I increased the pressure on her clit and then pushed my tongue as deep into her as I could go.
Courtney encouraged me by grabbing fistfuls of my hair and pulling me even more into her. She suddenly started shaking as the first wave of an orgasm washed over her.
“Don’t stop, don’t you fucking stop!”
My face was suddenly flooded as Courtney erupted, squirting clear, warm liquid over me and the bed.
As she was coming down from her climax, she said, “I’m sorry, I’m sorry. This has never happened to me before.”
I wiped away some of the wetness from my face and moved up and kissed her.
“Don’t worry about it,” I told her as I positioned my throbbing dick at the entrance of her pussy and in one stroke buried myself to the hilt in her.
“Oh my god, fuck, fuck!”
I asked if she was okay and she responded by thrusting up and squeezing me with her kegels.
I felt like my cock was gripped by a strong woman’s hand in a velvet glove. Her cunt was warm and wet, almost sopping. I relished the feel of her as I lay against her young body. Enhancing the whole experience was the fact we were on the bed I shared with my wife. And Courtney was wearing her lingerie and CFM heels.
I withdrew my cock until the head of my penis was the only piece of me in her.
Courtney squirmed, raising her hips to draw me in. “What are you doing?!? Fuck me!”
“Beg me,” I said. “Tell me what you want.”
“Please, give me your cock! Please fuck me!”
She kept lifting her hips and I heard the stiletto heels punching holes on my mattress.
I fucked her now as hard and fast as I could. I knew I couldn’t last long and I was right. I stroked into her until I bottomed out and then quickly withdrew. As my pace accelerated I was shaking the bed and Courtney cried out as I exploded inside her, emptying my cum into her. She erupted at the same time as I did, her orgasm racking her body. She once again released, actually squirting her clear and warm liquids onto me and the bed as we felt the high sensation of the orgasm we shared. She breathlessly apologized for the wet mess. I collapsed onto Courtney’s drenched body and rolled to the side.
“Don’t apologize.”
As we held each other she said, “That WAS incredible, I’m sorry I made a mess of your bed.”
I replied she had nothing to be sorry about and kissed her long and gently.
“Are you spending the night with me?” I asked.
“Absolutely.”
As we held on to one another, we could feel the wet spot Courtney had created with her newly found squirting episode. I suggested we change the bed sheets and she agreed. The moisture resistant mattress pad kept it dry and we quickly changed the bedding and settled back into bed.
The purple mark on her underboob had grown and was angry looking. I pushed the cups of the bra she was still wearing aside, and kissed her magnificent tits. At the same time, my right hand had moved to her red bush and I probed her steaming pussy with two fingers. She was breathing rapidly and rolled on top of me, grabbed my newly swollen cock and rubbed the entrance of her cunt before she impaled herself.
Courtney said, “Don’t Move.” She squeezed me with the walls of her pussy and slowly started pulling out until my cock nearly slipped out of her, then she buried my cock inside of herself again. She kept rocking until she was rapidly fucking me, to another soul-shattering orgasm.
“Oh fuck, oh god, I’m cumming again!”
As she rode up and down on my cock I erupted into Courtney again as she rode me cowgirl style. I hadn’t been with woman this young in years and decided I wanted this again. She was a fantastic fuck and it was made all the better knowing she had instigated our love-making. She lay on me as we tried to regain our breath.
After our love-making (or should I say, fuck-making), Courtney said, “You’re better at sex than the neighborhood ladies ever could have imagined. My friends are going to be so jealous.”
“What makes you say that?” I asked.
“I said it because you’re the best sex I’ve ever had. They won’t believe my hickey!”
We fell asleep in my marital bed as I spooned Courtney. My subdued cock felt perfectly wedged in between Courtney’s heavenly ass cheeks.
She woke me up at 4:00 a.m. by jacking my prick back to hardness, and the rest of the night only got better as she moved down and started licking the head of my cock. Taking her time Courtney gave me a fantastic blowjob. She started slowly, but was soon sucking with such skill I was ready to cum for the third time. I suddenly felt one of Courtney’s hands move under my ass and she pushed a finger into my asshole and inserted it knuckle deep. I had never experienced or expected this and I lost myself to one of the most intense climaxes I had ever had.
With Courtney lying beside me, I fell asleep again, When I awoke several hours later, she was gone.
Courtney left a note that read, “Thank you for the incredible ‘graduation’ present. Can we do this again soon? I hope Jan doesn’t mind, but I’m keeping the heels and lingerie. Oh, and can I bring my best friend Judy next time?”
End of Part 1