I finally loose my Virginity to an MILF

When his first sexual encounter goes wrong and reputation tarnish, a next door asian woman helps him gain it back."

I originally intended for this story to be short, but I wanted to make it longer. Enjoy.)

“This is my first-ever article on here, so some grammar mistakes and repetitive words as well. I’ll try my best to search for more complex words on the internet.”

April 20th, 2008, 10 a.m. It has been a year since I graduated high school (graduated on June 2nd, 2007, to avoid any confusion), and during that time, I moved away from my seven annoying siblings. My parents were quite freaky back in the day. 😏

I was the 2nd child to leave the nest after my older sister stayed in that hell hole until I reached junior year in high school. She studied to be a graphic designer for Microsoft.

This resulted in me finally getting my own room (moving into her room) until my mom gave birth to the seventh child. And put a crib next to my room.

Which marked a total of 9 children, including me and my older sister.

But back to the present day, I finally have my own house due to working in the food business. “I knew selling burgers and fries out of a busted-up truck was a successful idea.”

My name is Robert Winston. A Caucasian, 19-year-old man, with a blondish-colored bro flow hairstyle, 5’9” tall, 🍆 size small/2.5 inches.
And a virgin.

A year ago, in my final year of high school, I had a girlfriend named Veronica Mayday. She was the hottest girl in school. “I’m talking,” gorgeous dark pixie cut, tan-like skin color, ruby eyes, crispy and smooth lips, and was 0.3 feet shorter than me.

However, when we decided to get freaky in a motel room (because I had to share a room with a sibling, and anybody in my parents’ house could’ve heard us having sex.

At the motel, Veronica pulled down my pants. She laughed like a dolphin. And she said this:

“You called that your special paradise?!”

“Not even my older sister would suck this tiny shrimp. I’m leaving, and we’re through.”

Those words destroyed me, and the worst part is she wasn’t quiet about it. Since she was popular in school, she was quick to spread that my penis was small and not average in size.

Everybody in school laughed at me until our graduation. The worst part was that Veronica and her new boyfriend, Ace “the superstar,” exposed me at graduation, and it wasn't even true. That I had a foot fetish and I was into minors.

(Not a single minor in this story is involved in any sexual activities and they are only mentioned innocently.)

And everyone in town believed her and Ace.
The principal sent me and my entire family home, and both of my parents were disappointed in me. My younger siblings bullied the shit out of me, regardless of whether I was older than them.

People around the town were pissed at me and disappointed in me as well. All because I have a small dick.

Which leads to the present day, and people in the state of Oklahoma(that bitch posted the false prank and went viral) still remember that incident and despise me still. My food business actually flopped and was successful before the incident. I was smart enough to save all the money and invest in a house.

But now I don’t know what to do. Unexpectedly, I hear knocking from my front door, and I walk downstairs to see who it is?

I peek through the tiny hole in the door, and my heart pounded fast. My cock became erected where it almost pierced through my blue camouflage shorts.

A beautiful Asian woman with dark, wispy bangs, 6’1 feet tall, had double to triple D-size breasts and was wearing an emerald-colored backless jumpsuit. Her thighs, however, were somewhat small, but her cameltoe was clinched to the lower part of her dress, and her bottom was average in size.

She was holding a Louie von Ton purse and wearing a small navy blue fedora on her head.

“Can I help you, ma’am?”
In a questionable manner.

“Are you the young boy who has a foot fetish and targets minors for their feet as well?”

“(Of course, for fuck sakes)”

“No, lady. That’s not true. I’m not into minors, and I don’t have a foot fetish. Some chick that used to date in high school pulled a sensitive prank on me, saying that kind of nonsense, and now this entire person doesn’t want anything to do with me.”

The lady gave me a somewhat sympathetic face.

“I’m sorry to hear that, but the other neighbors don’t want you here anymore.”

Her response pissed me off even more.

“But I have only been here for 3 weeks. It hasn’t been a month yet.”

“I understand you, but they don’t want you in their neighborhood except for me.”

“Wdym?”

“I didn’t believe that idiotic woman because my friend told me you’re a good man (and he’s good-looking).”

“So what do you propose then?”

“I have a son who is a 7th grader in middle school. He’s a good kid just like you. However, he’s very isolated from the outside world and from me as well. Unfortunately, he’s been falling behind, and there’s a 40% chance he’ll get held back.”

“So I’m wondering if you can tutor him?”

Robert expresses a 🫤 face to the lady, signaling if he can do it or not.

“IDK if I can do it, especially with my current false reputation.”

“Please, sir. I’ll pay you handsomely to support your food truck business as well.”

I started to notice a little shed of tears coming from her eyes, but the way she mentioned my food truck business sounded like she wanted to be my sugar momma. I guess I’ll see how much she pays and see if it’s too much or balanced.

“OK, I’ll help your child with his classes.”
🙂

“Thank you so much, sir. May I have your name, please?”

(I thought she knew who I was?)

“I’m Robert Winston.”
As I proceeded to shake the lady’s hands, damn, her hands are hella soft.

“Lilith Thorne.”
She gave me a big smile.

“ I live 2 houses down to your right side, and I’ll see you tomorrow afternoon.”

“OK, Mrs. Thorne😁”

Mrs. Thorne left Robert’s front porch and went back to her house. Right when Robert was about to head inside, he saw Mrs. Thorne’s wallet on the front porch and assumed she must’ve dropped it.

Robert decided to take it to her tomorrow morning, but for now, he went inside and cooked dinner for himself.

Robert’s skill level in cooking was decent to good. Where his parents had stated that it was almost to die for, and his sister recommended opening a food truck and working his way up into opening a restaurant.

That was his dream, and to be successful in life, unfortunately due to his setup reputation, Robert had nearly given up on it.

He planned to clear his name and become a better chef in the future.

Robert was cooking a medium-rare steak with Brussels sprouts, a small side of tomato soup, and French fries. After an hour of cooking, he set up his table and forks, and finally, he destroyed his dish.
(He finished it under 30 minutes)

Nighttime had approached, and Rob did his gloaming routine. He brushed his teeth, fixed his hair a bit, and cleaned his face. After the hygiene part was done, he would set up his bed when it was time for him to go to sleep. He’d have an interesting tomorrow afternoon.

April 21st 2008, 3:00 in the afternoon had arrived and Rob headed to Lilith’s house to tutor her child and to return her wallet as well.

He was wearing a basic white shirt and blue shorts with black shoes.

When he knocked on her oak brown door, a young boy had opened the front door for him and was almost the same height as Rob.

A 13-year-old boy with the same eyes as his mother, but with noticeable brown eyes, a dark-colored two-block cut hairstyle, and was wearing a Dragon Ball T-shirt and orange basketball shorts.

“Is your mother around?”

“I’m not supposed to talk to strangers, especially Pedophiles!”

“(This shit is getting annoying)”

“I don’t touch minors…okay! Someone falsely claimed that I did those things and it’s not true.”

“Well, that’s a damn lie. I believe what Veronica says on her podcasts all the time, and my favorite NFL player says the same thing about it as well.”

“(That bastard actually made it all the way, and he was fast about it too. While Veronica became a podcaster, I guess they did tie the knot.)”

Rob couldn’t get Lilith’s son to understand his false accusations and was about to give up until Lilith herself arrived at the scene.

Rob’s heart started to pound hard as he saw what he saw.

Lilith was wearing medium-tight-level lime-colored leggings with a special type of sports bra (colored lime) that was able to be zipped open or closed in the center.

“Nakoa Thorne, you’ll stop disrespecting your tutor and accusing him of what he didn’t do!”

“(Nakoa…I’ll remember that)” 🧐

“But…mom?!”
😟tone

“Go to your room and wait for him to be there”

“Bu-“

“NOW”

Nakoa went upstairs to his room, while Mr’s Thorne approached Rob.

“Feel free to come in.”

“Thanks, Mrs Thorne”

Rob observed Lilith’s kitchen and her living room and it was ravishing

Rob enters Lilith’s house, and it looks nearly the same; however, it was bigger inside than outside. The kitchen looks like an average millionaire’s kitchen, with a 32 inch tv in the living room, while the couch looks like it was made with cheetah fur. The wooden floor looked like the pink-colored bush trees from Japan. The walls were painted white and were the same color as the ceilings.

“I apologize for my son’s behavior earlier. He’s easily influenced by the internet, which led to his grades in school diminishing.”
In a Sorrowful tone

“It’s alright Mr’s Thorne, I wasn’t aware that my ex had influenced your son through her misinformation podcasts.”

“You used to date that woman?!”

“I was shocked as you were when I had the courage to ask her out. Unfortunately we all know how that relationship ended”

Robert’s to get a little upset about the incident.

“to this day I envoy her and her boyfriend for pulling that stupid prank on me for no reason all because I have a small penis!”

Lilith became stunned when he heard Robert say the main cause of his false reputation.

“Is that what happened? When she pulled down your pants and saw your small wiener”

“Yes”

“I haven’t had the motivation or the courage to date another woman.”

“Interesting”
🧐tone

“I’m sorry I brought up my past trauma, anyway what’s my first task of the day?”

“Tutoring my son for at least 2 hours, and then I want to have a conversation with you in my room.”

“I’ll be in my room doing some yoga, let me know if you need anything or if my son is causing you any problems.”

I nodded at Mrs Thorne as she went upstairs to do her yoga. I decided to spend 5 minutes snooping around her house and my first target was the family photos, I needed know Mr Thorne was?

It only took me 50 seconds to find the family photos on a wall next to the front door. There were approximately 30 photos, but only 2 of them had Mr. Thorne in them. His head was ripped off, but only the body was there.

Did Mrs Thorne divorced him or was he abusing her to led to that divorce?

I spent enough time looking at the family photos, and I headed to her son’s room to tutor him. Her son was somehow the same height as me, and he’s only a 7th grader about to be an 8th grader soon.

5:00PM

Two hours have passed and day one of tutoring her son was a little problematic, he easily forgets the easy methods I show him and he mostly refuses to listen to me from time to time.

“I was going to snitch, but it was only the first day, so I let it slide. I left his room, which was next to the garage door. I headed upstairs to find Mrs. Thorne.”

Right before I found her door,I heard tiny but soft crying coming from her room, I assume she must’ve broken a bone or something?

A second before I knocked it. I noticed it crack open to where you can peep through it, in which I did to see what happened but it wasn’t crying sounds, it was her moaning.

My one eye peeping through it widened like an owl. She was slowly fingering herself on her queen size bed. However she was doing slowly and she looked aroused. (She might’ve also finish her yoga at a faster pace)

I didn’t see anything in her other hand, so she must’ve been doing it from her own mind or fantasy.

I was conflicted if I should head back to my house or watch this and hope I don’t get spotted.

But then again she needed to talk to me about something so I should probably just sit on her floor and wait.

Right when I was about to back away from her door I accidentally slipped and failed on my butt on her wooden floor and it made a thumping noise which alerted her.

This alerted her and she stopped masturbating to see what the noise was while still naked.

She open the door and saw me on the floor.
Her face instantly turned hot red.

“What are you staring at?!”
(In a shocked tone)
“I’m sorry Mrs Thorne I didn’t mean to stumble upon you like this I came for our conversation remember?!”

“I almost forgot that, about let me put on something at least.”

“Ok”

I felt ashamed at almost looking at her beautiful breast. I waited for a moment until she came back 3 minutes later with a light gray bustier bra and wearing a toned white thong.

I almost blushed hard but I prevented it from happening.

“Come inside please”
In a asking tone

I went inside her room and she closed the door behind me. Her walls were violet toned with black curtains covering her windows and a bathroom connect to her room as well. We both sat on her queen side bed and chatted.

“So I assumed this is the master bedroom?”

“It is and I’ve been in this room by myself for 3 years now.”

“You don’t have a husband?”

“My husband cheated on me with my younger sister, and just a year ago she even gave birth to his child. Moreover my son doesn’t know he has a younger sibling and it should stay that way until he reach high school.”

I felt sympathy for her and I didn’t want to know her ex husband’s name because it will boil my blood.

“I’m sorry to hear that, but if you don’t mind me asking how old are you?”

“I’m 35 years old and my sister is 13 years younger than me. I was married to that man for 14 years.”

“Our divorce is also the reason why Nakoa has been slacking In school as well.”

(Well that explains the problem why tutoring him today was difficult)

Suddenly Lilith starts to shed some tears.

“Mrs Thorne it’s alright to express your feelings, I can’t believe a dirty bastard like him will cheat on you, your beautiful body will want a man to stay with till the ends of the earth, you were a great wife and a perfect mother”

Lilith stopped crying and was stunned by Rob’s speech. Unexpectedly she then put on flirtatious smirk bitting her mouth.

“Your speech was very hot and sexy. You’re the type a man, a woman needs In their love life.”

She then proceeds to catwalk to me and pulls my shirt up to see my 6 pack abs and it turned her on. However I started to hesitated

“Woah… I don’t if I can go through with this?”

“Maybe this will change your mind”
She gave me a smirk and she took her bra off and her breast flashed me.

(I can’t believe I’m finally loosing my virginity for reals this time)

She finally took my shirt off and pluck her lips against mine and we started making out. She slid her tongue into my mouth and mine rubbed against hers.

Then she went close to my neck and proceeded to give me a juicy hickey. While with my right hand I grabbed her squishy and soft breast. And by heavens sake it felt like I was touching clouds.

A minute later we went back to making out with our tongues and then she decided to take it to the next step.

“I didn’t know your such a kisser especially a virgin one, (as she is rubbing my man abs) but I thinks it’s time for your key to unlock my paradise.”

I was a little confused about what she said but this side of her is similar to Veronica’s but if she was actually nice and understandable about things.

However I suddenly realized that the last I almost lost my virginity was when she saw my small dick, and now I am afraid if it’s going to happen again.

When Lilith motion her body to my underwear and pulled them down to see my 2 inch cock, she gave me a little smirk.

“What a tiny sword you have, I have something to make it sharper…IYK what I mean” (whilst making her smirk bigger)

She got off me and went to her bathroom to get something for it, 1 minute later she came back with a blue pill on the palm of her left hand and holding her pink panty with her other.

She casually tossed her panty aside and extended her left hand, offering me the blue pill.

I didn’t question what it did but I took it and look at her face with a questionable face. I swallowed it (I guess that’s what you do with a pill?) and after a good minute I felt strong vibrations inside my cock and it went up from a 2 inch to 8 inch in 5 minutes.

Lilith look directly at my now erected penis, she motion me to stand up from the bed and she whispered into my ear.

“This will be an unforgettable night of your sweet and innocent life. I’m going to suck the living fuck out of your testicals, I’m going to drink every last drop of your children and put them inside my hungry mouth. And I won’t hold back.

A second before I can respond she bends on her knees and starts sucking my cock. She doesn’t start slow but at a fast pace and she speeds it up as she goes back and forth on it.

I tried to withstand her amazing blowjobs but I already felt my semen reaching the tip of cock and I was about to explode inside her slimy but juicy mouth.

2 minutes go by and I still held on but she kept increasing her sucking strength. I tried to hold it back to release a huge load but it was already too late and I release a huge load of cum in Lilith mouth.

Whilst cuming inside her mouth she was swallowing every last ounce of it and this went on for 15 seconds until I ran dry.

I drop on her bed and I immediately got knockout when she join me I saw her with semen all over her mouth and lips. She whispered something into my ear.

“I want that little sword 4 times a week every time you’re done tutoring my son. Each time we do this you’ll never get bored of me and my pink pussy.”

That aroused me hard but unfortunately my cock turned into an elephants nose.

She cuddled against me and wrapped her leg around mines which was close to my now drained cock. She also gave me a tiny smile and slowly went asleep. Resting her head close to my neck and shoulders.

Reflecting on my past sexual encounter with Veronica, I chose to leave it behind. I no longer worried about my size; instead, I found satisfaction and pride in it.

Finally, I rest my eyes.

The end 😌