Stephanie was always too young for me, growing up. I was 18, she was 13 — it could never work; not at the time, at least. Even as we got older, she was cute — strawberry blonde hair, freckles — but always just a little out of my age range.
I remember her mother always telling me, “She has the biggest crush on you!” and wanting to take pictures together whenever we were with a group of people. For the most part, it was pretty obvious — always smiling around me, hugging me, telling me she loved my cologne — but it was still cute. She was just too young.
One night, I was getting off of work and my friends asked me to meet at the local hangout, so I headed over. There was some kind of celebration or something going on in the dining area because Stephanie, now 18, and a bunch of her friends were all dressed in a more of an upscale-dinner attire than the restaurant requires. I walked past the party and met up with my friends, some of whom were bartending in the other room.
When the party was over, some of the parents came into the bar area to hang out and celebrate some more while most of their kids — Stephanie included — drove other girls home.
I always got along with Stephanie’s mom; Diane was definitely a “fun mom” and way more laid-back and casual than some of the other parents. By the time we started talking, I could tell that she was a little buzzed, as was I. We were catching up about what I was doing, what Stephanie was doing college-wise, etc. and my best friend, Jeff, excused himself from our circle to use the bathroom.
Diane turned to me and whispered in my ear, “We should totally fuck with him when he comes back.” Intrigued, I replied, “And how do you say we do that?” She started to talk, chuckled a little bit, then finally spit it out, “When he comes out, you should just kiss me.” I laughed out loud for a couple of seconds until I realized that she was completely serious. “Fuck it, why not?” I said, and we kept our conversation somewhat casual for the next few minutes.
As Jeff walked out of the bathroom and started heading back towards the bar, Diane looked at me and said, quietly, “You ready?” I smirked, and nodded. She then grabbed my face and planted one on me. After a couple of seconds, I tried pulling my head back, but she didn’t want to stop. The next thing I knew, her tongue was in my mouth and mine was soon in hers.
Everyone in our group now stopped to look, but Jeff stood there, stunned. “What the fuck was that?!” he said, in a jokingly confused manner. “What? He’s hot,” she said, still hugging me. I just shrugged and smiled.
Once the moment was over, Diane headed to the end of the bar to talk with my friend Paul, who was bartending. My other friend Stephen was already down there talking to him. Diane went to the bathroom shortly after, so I went to say hello to Stephen.
“Dude, who is she?” he asked me. “Long story, man,” I cracked back. He said to me, “This woman comes over here and just starts saying, ‘I just made out with that guy over there,’ then goes, ‘I’m totally going to fuck him tonight.’”
I didn’t read anything into it. There was easily two decades separating us and her daughter liked me; she would never do anything, knowing that. At least, that’s what I thought.
She came back and asked for a light for her cigarette, which nobody had. She said she had one in her minivan, so she asked if I’d take a walk with her. I saw Stephen and Paul smirking out of the corner of my eye, so we walked out the back door to the parking lot.
Once we turned the corner of the restaurant, she pinned me against her car and started kissing me. “I take it we’re not fucking with Jeff anymore?” I joked. She slid her hand down my chest until she was massaging the lining of my cock in my jeans. “No, sweetie, we’re not,” she said, biting my lip.
She opened the door and started pushing me into the backseat. Once we were both in, she started grinding on top of me. “So, when was the last time you had a blowjob?” she said. I paused. “It’s been a while,” I panicked. “Let me tell you — kids today, they don’t know what the fuck they’re doing when it comes to giving good head. They think that just because they put their mouth on a guy’s cock, that’s going to make it cum.”
In a weird way, it was turning me on. My cock was so hard now that it was actually starting to hurt from being pushed down in my jeans. It felt like my dick was going to snap in two if I didn’t move it, so I unbuttoned my pants and took it out. Diane looked down and grabbed my cock, slowly jerking it while she twirled her tongue around mine.
I shifted my body to get in position and Diane pulled my pants down to my knees. Her lips were inches away from the head of my cock as she held it, looked at it, and said, “You know, my daughter isn’t the only one who’s thought about this.”
As my shaft throbbed in her hands, she wet her lips and slowly put my cock into her mouth. It was arguably the best blowjob of my life, but I was still freaking out a little bit. Diane noticed, so, she was blunt. “Relax, you’re getting your dick sucked.” So, I did. When I heard that, I closed my eyes and made my body go limp with relaxation.
Stephanie looked so much like her mother that I kept going in and out of visualizing her being the one sucking my cock. Once I started getting into it, I noticed that was slowly thrusting in her mouth, which caused her to gag a little. After about the fifth time, she cracked, “You’re not fitting this whole thing in here.” I opened my eyes and apologized. “Sorry, I didn’t realize I was doing it.” “Yeah, and I didn’t realize you were this big.”
I’ve never had someone use so much tongue during a blowjob — in her mouth, out of her mouth; it was incredible. My favorite move was when she would continue licking back and forth when slowly coming up my shaft. She pulled me out of her mouth, briefly and asked if I had a condom. I reached into my jacket pocket and pulled one out.
“Good, because I’m soaking wet over here and if this cock isn’t in me soon, I don’t know what I’m going to do with myself.”
I slid the condom on and positioned her over the seat. I lifted her dress up and pulled her panties over her incredible ass. I slowly guided my cock into her. “Oh, Jesus fucking Christ,” she moaned, breathing heavily. “I had that thing in my mouth and I still wasn’t expecting that.”
I shoved my entire cock in her, right down to the base, and she let out a small wince. I slowly pulled back, then shoved my cock in her again, this time giving her a firm slap on the ass.
She reached back and grabbed my shirt. She arched her back and turned to me. “Did I say you can slap my ass?” Without hesitation, I snapped, “Did I ask?” before slapping her again, now grabbing her ass afterwards. She took a deep breath and sighed, “Kids today — no fucking respect for their elders.” I grabbed her hair and pulled her back to me, “Excuse me, ma’am… do you want me to fuck you or not?”
I still couldn’t believe how wet she was, or how hard I was. I grabbed both of her hands and put them behind her, holding them down against the small of her back. The harder I began fucking her, the more into it we got. “Oh God, I’m gonna— gonna—,” she panted. I slammed my cock into her and kept it in as she moaned. “Cum!”
Her legs started shaking in an involuntary spasm. I leaned over her to kiss her neck, while reaching down to rub her pussy while I was still inside her. She started to shake again as I rubbed her clit. I started to thrust again and she came almost instantly.
I grabbed both of her wrists with my left hand and smacked her ass again with my right. After a while, her ass cheek was nothing more than a giant red handprint.
I started slowing down to catch my breath and freed her hands from mine. “Alright junior, now it’s my turn,” she said, pushing her hand against my chest again. “Sit down,” she said in a demanding whisper. She threw her leg over me and started to rub my cock with her hand. “Let me show you how a real woman rides a dick.”
She slid my cock into her, putting her arms over my shoulders and the seat. I pulled her dress up and lifted it off her body. I unhooked her bra seconds later, until she had nothing but her shoes and makeup on while sitting on my cock.
She started working her hips, grinding her clit against me while grabbing her tits. I cupped her ass in my hands as she continued to gyrate on me. I leaned in to try and kiss her and she pushed both hands against me and pushed me back to the seat.
“Oh no,” she sighed. “You stay right there.”
Since she wouldn’t let me touch, I reached back behind me and grabbed the top of the seat and continued to thrust my cock harder into her. “You’re going to cum, aren’t you?” she sighed. “Oh my God, yes!” I moaned.
“You’re not going to tell her, are you?” she panted, slamming her pussy on my cock. “No… no… no,” I breathed. “Cum for me, Zach — cum in me, Zach.”
I squeezed the seat and started to thrust harder. My ass was now up off the seat and had lifted her higher, on top of me. “Now you stay there,” I said, starting to climax. I couldn’t stop thrusting. The build up of my orgasm was one of the most intense I’ve ever felt. I started cumming, and for once, I was louder than the woman.
“Ugh… ugh… Oh fuck!” I yelled, busting inside of her. “Holy fuck!”
I continued breathing heavily for the next couple of minutes as I tried to come down off the post-orgasm high. She leaned down on top of me, also out of breath and dripping in sweat. “You know Stephanie would kill me if she ever found out, right?” she chuckled. “Well, I can keep a secret if you can…” I said.
I pulled my pants up and walked to my car to head home. The next morning, I got a text from an unrecognized number. “Zach?” “Who’s this?” “It’s Stephanie’s mom, I just wanted to make sure it was you.” “Is everything OK?”
“Stephanie’s car didn’t start, so she took the minivan to school… she asked why there was an opened gold Magnum condom wrapper in the backseat.”
I figured it was best not to answer that one.