As a kid, my parents moved around cities due to work, which meant that I went to several schools and found it tough to make friends. I was never able to get comfortable in school or at home, as I never knew if we were going to move again. It wasn’t until I was in the fifth grade that we settled down and that was when I met my best friend, Lewis Brown.

Lewis and I became inseparable and basically did everything together as it helped that we lived right down the street from each other. That went on until we were old enough to go out on dates with girls. He got hooked on a pretty girl and it sucked because it was like her and I were fighting for Lewis’ time. I didn’t interfere with what they did, but I did feel left behind as I wasn’t dating anyone.

Now, as a seventeen-year-old, I was still having trouble getting along with the opposite sex. I was terrible at talking to them and even worse at attempting to get a simple date to the movies or to a school event. It was really frustrating, and it was something that was on my mind day and night.

I figured it was a good idea to have a wingman for the whole dating thing and who better than my best friend, so I went looking for him to see if he was available for the night.

I rang the doorbell and, as usual on a Friday night, his mom, Mrs. Brown, answered the door, “Hey, Paul, looking for Lewis again?”

“Yeah, that guy is never around these days,” I said with a smile and a quick look at her breasts in her blue tank top.

“Believe me, I know,” she said, smiling back. “But anyways, you care for some cupcakes?”

“Yeah, always,” I said, entering the house.

Walking behind her, I noticed I could see her dark panties through her white capri pants.

“Damn, is she wearing sexy panties,” I thought, forcing myself to look away.

We sat down and I got a cupcake while she served herself a glass of wine. We talked about the usual stuff but mostly it was about Lewis and his girlfriend. When she got frosting on her lips, I tried ignoring it, but my lustful brain made my eyes focus on how her tongue licked it clean.

“Dude, what the fuck are you doing,” I thought, trying my best to move those thoughts aside.

It was a challenge to remove those thoughts since she was a lovely woman with a delicate face and captivating eyes. She also had the sexiest strawberry blonde hair and a body that put women half her age to shame. Her soft and light skin made my heart skip a beat every time I came in contact with it but even if I didn’t like to admit it to myself, her round ass was my true weakness.

“The cupcakes are great like always,” I said, getting up to put my plate in the sink.

“You know they’re specialty,” she said.

“So, any idea what time Lewis will be back?” I asked, looking at the time on my phone.

“No clue, probably once he gets lucky,” she joked with a smile.

“Yeah, I guess so,” I said, smiling but surprised at her joke.

“And what about you, Paul?” she asked.

Seeing her fill her glass of wine, I asked in response, “What about me?”

“You gotta have a lady or two you haven’t told us about,” she said.

She brought the glass up to her lips and took a drink while she waited for my answer.

“Uh, no, I don’t, unfortunately,” I replied.

“You sure?” she asked.

“Yeah, I’m positive,” I said. “If not, I’d probably be out on a date myself.”

“I’m just teasing you, Paul,” she said. “But the ladies are missing out.”

Following along, I said, “That is true, definitely true.”

Shortly after that, I left and was already halfway back to my home when I realized I had somehow forgotten my phone. I turned back to the Brown’s house and briefly checked out a couple of teenage girls walking on the other side of the street.

I rang the doorbell and looked at the Easter decorations in their front yard while I waited for Mrs. Brown to answer the door.

“Hey, what happened?” she asked, not fully opening the door.

“I, uh, forgot my phone,” I said.

“Ah ok,” she said, reluctantly opening the door to let me in.

As I walked in, from the corner of my left eye I could see that she had already taken off her pants to get more comfortable. I grabbed my phone from the kitchen counter and then turned to see her by the coffee table in just her tank top and panties.

I took a glance of her and thought, “Lace and mesh, she really is wearing sexy panties.”

She must have caught me looking because she asked, “Um, found your phone?”

“Uh, yeah,” I said, slightly raising my phone.

“And, um, sorry but as you can see, I already got comfortable,” she said.

“No, it’s okay,” I said. “I just needed my phone.”

On my way to the door, she turned around seemingly without thinking twice, and picked up her phone from the table. That gave me a perfect view of the cheeky mesh back of her panties and how it was being eaten by her shapely ass.

Standing there frozen, looking at her mostly bare ass cheeks, I thought, “She’s just amazing.”

She turned to face me and definitely caught me looking this time.

“You okay?” she asked, sounding and looking as innocent as ever.

Feeling my face getting hotter by the second, I said, “Yeah, uh, I’ll be on my way.”

To my surprise, she said, “Alrighty then, you naughty boy.”

Trying to explain myself and somehow make it less embarrassing, I said, “I, um, I couldn’t help myself.”

“It’s okay, you’re old enough to appreciate a woman,” she said, walking towards me and putting down her glass of wine on the coffee table.

“No, er, you’re such a tease,” I said with a smile, trying to defuse the situation.

“I’m serious,” she continued. “If Lewis is old enough then so are you.”

“What does that, uh, I don’t follow,” I muttered.

She came up to me and ran her palm very close to my groin.

“What, er, are you doing Mrs. Brown?” I asked.

“I know you fancy me, you always have,” she said, caressing my growing bulge through my shorts. “Let me give you an early birthday present.”

“I, er, I think that, too much wine,” I muttered to no use.

She put her left index finger on my lips and said, “And call me Kayden from now on.”

Without hesitating, she quickly sat me down on the couch and tugged my shorts down to my ankles. Then, she got on her knees and kissed her way up my thighs until she reached my groin. Her fingers hooked under the waistband of my boxers and slowly pulled them down. My erect cock sprung free right in front of her and just like that my biggest fantasy was coming true.

“Very nice,” she said, grabbing my shaft and eagerly wrapping her lips around my head.

I couldn’t help but moan lightly at the feeling of getting a blowjob for the first time. Her mouth felt so warm and wet, which was something Lewis had raved about when talking about his girlfriend.

She stroked my shaft and sucked tightly on my head, giving me an intense feeling that was greater than anything I could have imagined. She then moved her hand down between her legs and began taking more of my cock into her mouth. Her lips reached lower and lower until making contact with the base of my cock.

“Oh fuck, she’s a fucking expert,” I thought as I remembered Lewis saying that his girl never tried to deepthroat him.

She nearly made me cum as she lightly bobbed her head with my entire cock in her mouth. She then slowly let me out of her mouth and looked up at me with her watery eyes.

Catching her breath, she said, “It’s been a long time for me”

Looking down at her green eyes, I said, “My first time.”

“I know,” she said, pausing to lick the length of my shaft. “I’m not gonna be like those girls missing out.”

While she stroked my shaft and caressed my balls, I said, “But I, um, don’t know why you are doing this.”

“You’re a special guy,” she said, tightening the grip on my shaft. “That’s why.”

By this point, my cock was so engorged that my head was a unique purple shade. Precum oozed out of my tip thanks to her tight grip, and I knew it wouldn’t be long before I was spurting my load of cum. Then, as she resumed sucking on my head, my eyes fixed on her jiggling breasts and my hands reached to caress them.

“Fuck yeah! She doesn’t mind,” I thought.

I fondled her breasts eagerly and then pushed my luck by helping her get on the couch with her ass up in the air and right to the side of me. I ran my hand all over her round ass and just couldn’t get enough of how incredible it felt to touch. I could also feel the heat coming from between her legs, so I knew it wouldn’t be a problem if I moved her panties aside to rub her pussy.

After doing just that, I coupled my index and middle fingers to run them up and down the length of her pussy. I traced her opening with my fingertips then slightly moved my hand further so that I could push my fingers inside of her.

“Mmmm,” she moaned with my cock in her mouth.

Her pussy hugged my fingers nicely and there was nothing that was going to stop me from fucking her sooner or later. I needed to lose my virginity and her pussy was just perfect for that. For now, I settled for alternating between fingering her and rubbing her clit, which she seemed to really enjoy.

“I’m…I’m gonna come,” I warned her, feeling her hot pussy juices running down my hand.

She sucked even harder on my head and stroked my shaft faster like a slut who was starving for cum. Of course, knowing that she was my best friend’s mother made it all that much fucking hotter. It was a dark fantasy but there was no way anyone could blame me.

“Mmmnnggg,” I groaned, pushing my hips up and erupting my hot cum into her wet mouth.

As I spurted ropes of cum into her mouth, I furiously rubbed her clit and made a stream of hot juices come out of her pussy.

“Fuck, I just made her cum while she was swallowing,” I thought, feeling proud of my first sexual encounter.

She let my cock out of her mouth and proceeded to lick it clean before saying, “That was yummy.”

As she looked at me, I brought my wet fingers into my mouth to get a taste of her and then said, “Very yummy.”

“You naughty, naughty boy, Paul,” she said, surprised at what I had just done.

“Not as naughty as you, Kayden,” I said, marking the first time I ever called her by her first name.

“I don’t know, you made me cum so good for your first time,” she said with a smile.

Feeling more confident and daring, I proposed, “Then let’s have a second time.”

“Of course,” she said. “But for now, we gotta get dressed before Lewis gets home.”

After getting dressed and cleaning up, I grabbed her by the hips and pulled her closer to me to plant a kiss on her lips. She pushed her tongue inside my mouth, and I grabbed two handfuls of her ass through the thin fabric of her white pants while we tongue kissed like lovers.

“You’re my fantasy,” I confessed to her.

“Oh, Paul,” she said, tongue kissing me before continuing, “You are very special to me, but we have to be very careful and don’t let anybody ever find out.”

“Yeah, don’t worry about that,” I said.

After that and a few more kisses and grabs, I left the Brown house for the second time in the night but this time it was a much sweeter feeling walking down the street. It was like I was doing a victory lap and how could it not feel like that when I thought of all the fun I would be having with Kayden.

In the following days, I told Lewis that I’d gotten lucky and was finally able to talk about a sexual experience of my own with him. Yes, in the back of my mind I felt guilty that my experience had been with this mom, but I found comfort in knowing that it was his mom who approached me in such manner.

I dealt with that conflict for a couple of weeks and in that time, I even started shamelessly checking out my own mom, as sex and lust took over my mind. My mom was also an attractive woman, a milf, but I had always ignored that until now. I started looking at her body in a sexual way, especially because of how much her ass resembled Kayden’s. I knew it was wrong to think that way of my own mom, but just how much worse was it than my new relationship with Kayden?

The night of my eighteenth birthday, Kayden drove us to an already reserved hotel room on the other side of the city. That was after she attracted all my attention at my birthday party in her red backless dress, which had straps that supported the high-rounded neckline and crisscrossed over the open back. The bodice was fitted at her waist and below it featured a short, flared and scalloped skirt.

“I couldn’t get my eyes off you,” I told her.

“I know, what a naughty birthday boy,” she said. “And you haven’t seen what I have underneath.”

“You are a great tease,” I told her, placing my hand on her bare thigh and caressing it.

“I planned all of this just for you,” she said.

When we got out of the car, I followed her and her clacking red heels through the parking lot as if we were mother and son. Anybody watching would have thought we were just that if it wasn’t for her quickly lifting her skirt to show me the red strappy cheeky panties she was wearing.

The wait in the hotel lobby felt eternal for me, as I was dying to get her out of that dress. At this point, I was fully marveling at her shoulder-length strawberry blonde her and at the contrast of her sexy red dress and her soft, light skin.

I continued eating her up with my eyes, especially her legs and feet, as I followed her all the way down to our reserved room.

Once inside, I lifted her dress and eagerly grabbed handfuls of her half-covered ass while our tongues met again. I then reached up her back to unzip her dress and moved the shoulder straps aside to let the dress fall to her ankles.

Standing there, naked except for her strappy panties, she stepped out of the dress and grabbed my hand to lead me to the bed. With my eyes fixed on her bare full breasts and pink nipples, she straddled me and smiled before pulling my shirt up over my head and removing it. She then got closer to kiss and lick the side of my neck and crawled her way down my body to take off my shoes and socks. Finally, she unzipped my jeans and pulled them down, leaving me with only my tented boxers.

I looked at her expectantly and she didn’t disappoint when she got on top of me in the sixty-nine position with her soft ass cheeks over my face. The aroma of her pussy filled my nostrils and my tongue was ready to get a real taste of her previously forbidden wetness.

I moved her panties aside and gave her hot slit a long lick, just like I had fantasized many times of doing. I spread her lips and gave her another long lick, but I again stopped short of making contact with her engorged nub.

She gently bit my cock through my thin boxers and then ever so slowly pulled them down, which caused my cock to bounce right under her mouth. She grabbed my shaft and repeatedly slapped my head on her flat tongue.

I placed my hands on her ass cheeks and pushed them upward to begin tracing her pink lips with my tongue. I did that a few times before swirling my tongue around her tight opening.

She placed her hands on my thighs and took my head into her mouth, sucking on it a bit then moving down to deepthroat me. Her saliva drooled out of her mouth and onto the base of my cock.

I pushed my tongue into her pussy as much as I could and swirled it around, which she seemed to like by the sound of her moans. I lubricated my thumb on her pussy and moved it up to rub it over her puckering asshole.

Plopping my cock out of her mouth, she said, “Lick it, honey.”

Not having to be told twice, I moved my tongue up to her asshole and licked circles around it.

“I’ve wanted this for so long,” she said at the feeling of my tongue flicking on her asshole.

Like in our first encounter, she gripped my shaft and stroked it in a counter-clockwise motion while she sucked on my head.

I kissed her asshole and gave her a long lick with my flat tongue until I reached her erect clitoris. I gently placed my tongue on it, and she immediately began grinding her hips to stimulate herself on my tongue.

“Mmmmm,” she moaned, without pausing her pornstar-like blowjob.

I grabbed her ass firmly to keep her in place and take control of her pleasure. I began relentlessly lapping, swirling, and flicking my tongue on her clit. I was a novice, so I resorted to what I had read on the internet about cunnilingus.

It wasn’t long before her sweet pussy juices ran down into my mouth, which made...