Jessica had just moved out of her home and was struggling to make it on her own. She was eighteen years old working as a waitress and a barista to try and make ends meet. Things were so much easier just a few months earlier. She was living at home and she was still in school. She missed her parents, her social life, her long free days, and the ability to masturbate at her leisure. Sure, she could masturbate now, but she was always so drained at the end of the day. Jessica barely had enough money to enjoy herself after paying her bills and putting some away in her savings account. Adult life was turning out to be a real bummer.

On top of everything, Jessica was lonely. Her friends all went their own ways and her coworkers were miserable. The only things that kept her company were her calico cat Marshmallow, her vast stuffed animal collection, and various online chat rooms. It was as if the world forgot about Jessica. Then one day Derrick messaged her.

Derrick was an old family friend. He was her father’s best friend who would always be included in their various family activities, at least until Jessica started to get older. He was roughly 39, a few years younger than Jessica’s dad. He would always spoil her and bring her all sorts of presents growing up. Derrick always seemed to make time for Jessica compared to her workaholic father.

Jessica read the message and the two entered a conversation:

Derrick: Hey Jessie. How are things? It’s been awhile.

Jessica: Things are ok I guess. Just trudging along. What about yourself?

Derrick: Oh God, where do I begin? Ida and I are getting divorced. It’s rough and she’s trying to take all of my stuff. Other than that though I’m ok.

Jessica: I’m sorry to hear that.

Derrick: Don’t worry about it. I’m all good. Now what do you mean by trudging along?

Jessica: It’s just that I’m working all the time and I’m lonely. Not too many smiles going around these days.

Derrick: Aww we’ll have to change that. How would you like to come over tomorrow night? We could order a pizza, play a game, and even maybe watch some movies. We could catch up too.

Jessica felt a little weird about it, but she knew it would be fun. It almost sounded like he was asking her on a date, but that would be silly. He was one of her oldest friends. She knew she could trust him. It sounded like exactly what she was needing.

Jessica: Yeah! Of Course! What time?

Derrick: I could pick you up around six maybe?

Jessica: Sounds great!

Jessica then sent him the address to her apartment and some directions. Derrick replied with a gigantic smiley face.

After microwaving and eating a burrito, Jessica cracked open one of her cheap romance novels and tucked herself in on her thin, uncomfortable mattress. She got to the point where the characters were confessing their feelings to each other and then she passed out.

…

Jessica just got off of her barista shift and rushed home to freshen up before Derrick would be over. She changed into some dark denim skinny jeans, some cute black sandals and a comfy pink blouse. She put some messy waves in her auburn hair and put on a little bit of makeup. Casual, yet cute and that was good enough for Jessica.

She left out plenty of food for her cat. Then she looked out the window for a few minutes and butterflies frenzied in her stomach as she noticed a red SUV pull up outside. Her phone beeped and she saw that Derrick was letting her know bağdatcaddesi escort he was here. She locked her door and rushed down the stairs. Derrick got out and Jessica gave him a great big hug.

“Hey, I missed you,” she said

“I missed you too. Are you ready for tonight?” Derrick replied.

“I sure am!”

Jessica loosened her hold on Derrick and took a few steps back. She took a good look at him. He looked really good for a 39 year-old. He had sharp blue eyes and only had a few grey hairs in his thick dark hair. He was pretty fit as far as she could tell and taller than she remembered. He was wearing a green button up shirt and some slacks. Jessica almost felt under-dressed. He was wearing a bold scent that Jessica delighted in.

“Just hop on in sweetheart,” Derrick said as he opened her side door, staring at her ass as she climbed in. “It looks like I only live about half a mile away from you, so we’ll be there in no time.”

After some light conversation they were there. Derrick lived in a two-story, dark-grey house in a small neighborhood. There was a black iron fence around his home with beautiful leafy metal work. Derrick held Jessica’s arm as he invited her inside, closing and locking the door behind them. The living room was sizable with beige carpeting, a love seat and some matching chairs were in the middle of the room. A wide television set on top of a dark wood stand faced it. There was also a bookshelf against the wall and fireplace at the other side of the room. Other than that, the large room was a little under furnished.

“This is a nice place you’ve got here” Jessica said.

“Well, I like to try,” Derrick replied.

“It’s just so comfortable.”

“Well I’m glad you’re comfortable here.”

“Come, sit down,” he said, gesturing to the love seat.

Jessica sunk into the puffy cushions. She sprawled out playfully and let out a little yawn.

“So what kind of pizza do you like?”

“Pepperoni and mushrooms.”

“Mushrooms? Tsk tsk. Just kidding. You’re my guest,” Derrick said laughing.

Derrick ordered the pizza and when it got there, the two ate their fill of the pizza, and they made a small pallet in front of the couch from blankets and pillows. They laid next to each other and watched some old reruns of a sitcom Jessica could barely remember.

“How about some strawberry ice cream? I hope it’s still your favorite,” Derrick asked.

Jessica confirmed, “Yeah I still love the stuff. I’m mostly full, but I could always go for a bowl of strawberry ice cream.”

David smiled and went into the kitchen. He came back a few minutes later and brought a bowl of strawberry ice cream with him that was topped with whipped cream and two cherries with two spoons at opposite sides of the bowl.

“I hope you don’t mind sharing a bowl, I like to cut down on dishes when I can,” Derrick said.

“That’s fine, I don’t mind sharing a bowl with you, what’s a few germs between friends?”

The two laughed and Derrick sat down next to Jessica. He took one spoon and made sure to get a scoop of everything. He then slowly guided the spoon to Jessica staring into her warm brown eyes. Jessica opened her mouth and pressed her lips against the spoon taking in the ice cream. She didn’t break eye contact. When she swallowed, Derrick smeared some more ice cream over her lips and leaned in. He then licked her plump, pink lips.

Jessica opened her mouth again and started beykoz escort licking his tongue. The two locked lips and their tongues wrestled for a few minutes, occasionally pulling away and exchanging hot breathes with lighter kisses.

“This is nice right?” Derrick asked her.

“I like it. I wasn’t expecting this, but I like it. I haven’t kissed a boy, er I mean a guy since I was sixteen,” Jessica replied shyly.

“I’ve been dreaming of this. Do you want this? Are you brave enough to see where this goes?”

“I do and I think so.”

“Oh Jessica, I was hoping you’d say that. Let’s go upstairs!”

Derrick grabbed her soft hand and Jessica followed behind him as he rushed up the stairs. They went into his bedroom which was very dimly lit. They sat together on the cool, white bed and kissed for a while longer. Then Derrick took off her clothes piece by piece lightly tossing them aside. Derrick took off his shirt, but Jessica unzipped his pants and took them off along with his tight boxers.

Jessica admired Derrick’s shape and the lines running along his muscles. She loved his hairy chest and even liked his trimmed pubic hair. Jessica had never seen a dick in her entire life. Sure she’d seen pictures of them, but not a real one right in front of her before. Derrick was big too and fairly erect. Jessica was a bit shocked

Jessica’s ample curves and pale breasts stimulated Derrick. He was amazed at the softness of her skin. He delighted in her hand-filling breasts, her plump ass, her toned legs, and of course her delicious pink and lily white pussy.

She laid down on the bed and Derrick climbed on top of her, putting all of weight on her. They kissed and Derrick then made a trail of kisses from her neck to her breasts. He suckled and licked the right one first and then the left one. He alternated between the two. He squeezed the opposing nipple when his mouth was on the other one. Jessica winced and let out a small noise, but she loved it.

“Are you scared?” Derrick asked.

“Yes and no. I like it, but I’ve never done anything like this before. I don’t know what it’ll be like.” Jessica whispered.

“Don’t worry, you should like this part at least, and after that I’ll be gentle.”

Derrick kissed her stomach and licked her skin, slowly making his way to her pussy. He kissed her other set of lips and pushed his tongue between them. He teased the inside of her strawberry lips and slowly licked her clit, then he started to go faster. Jessica moaned and ran her fingers through his hair. He added suction with his lips and Jessica was in ecstasy. Then Derrick withdrew his tongue and slipped a finger in her, then two. She squeezed around them. He pulled them out and plunged them back out while she moaned. He repeated until she was wet and Derrick decided she was ready.

He climbed back on top of her and kissed her passionately again with his erection stabbing her clit. He rubbed his wet fingers on his cock and gradually drilled inside her tight, pink walls.

“Oh Derrick.” Jessica wailed.

“Shush” Derrick smiled holding his fingers to his lips, licking them after.

He pulled out and thrusted, and then pulled out and thrusted again. Her gasps and moans were matched by his grunts as the two made an animalistic song together. Derrick grasped her bare legs and lifted them, settling them against his chest. He went faster this way and her pussy became a wet mess, shamelessly leaking onto the bed sheets. caddebostan escort Derrick pulled on her breasts, digging his nails into them. He then leaned closer to her and let her legs return to the sides of the mattress. She embraced him, digging her nails into his back. Her bit into her neck hard and sucked on it. He made sure it was hard enough to leave a dark bruise later. Jessica cried out in pain, but she was so horny and filled with adrenaline that it felt amazing. Gushes of liquid came out of her pussy as she climaxed in true magnificence.

Derrick built up a nice pace and felt like he too would cum soon. He really, really wanted to cum into the girl he’d been fantasizing about since her last birthday. The one he pictured while fucking his wife and a few others for the past months.

“Can.. I.. cum.. inside you?” Derrick asked thrusting and pleading.

“Oh I don’t know,” Jessica said.

“Please? Don’t you like this? It’ll be the best part. You’ll make me very happy if you say yes,” he said looking into her eyes. “I love you,” he whispered, with a little shame.

“Yes, yes. Wait, what?”

With that he came inside her, his cock spitting cum deep down her hole. He didn’t pull out until he thought it was done planting his seeds. His forehead was sweating, his legs were shaking, and his breathing was labored. He flipped over onto his back next to her and stared at the ceiling.

Jessica was flushed and a mess. She put her fingers over her pussy and picked up some cum. She brought it closer so her eyes could see it as she stretched between her fingers. Jessica was aching and her pussy was burning, but she was immensely satisfied. She just gave her virginity to a man more than twice her age. A man she and her entire family trusted.

Jessica closed her eyes and asked, “Does this mean I’ll get pregnant?” Jessica quivered almost in panic. She shed a tear at the thought of becoming a single mom. Her family would be so ashamed and her life would become twice as hard. The misery would be unbearable. Her mind was screaming, ‘why did I say yes?’

Derrick noticed she was starting to cry, “Hey don’t worry about it. You won’t get pregnant I promise. Please don’t cry sweetheart. Here, let’s get you cleaned up.”

He took her to the bathroom adjoined to the bedroom and turned on the faucet to fill the tub. As it was filling up, he got on his knees and scooped some of the cum out with paper towels until it wasn’t leaking anymore. He then took a wet, warm washcloth and cleaned it all out from her pussy. Then with a second one he soaked up the tears on Jessica’s face and put his hand on her face, stroking his thumb on her cheek. He then threw the washcloths into the laundry basket near the bathroom closet.

“Everything’s going to be ok. I’ll take care of you ok” he said with confidence.

Jessica, although doubtful, smiled at him and tried to stop crying. Derrick then stepped away and started to mix in some bubble bath with the warm water until it was filled with bubbles. He guided her into the tub and she laid in it.

Jessica asked, “Aren’t you going to join me?”

“No, this is just for you, but I’ll help make you squeaky clean. Then, after that I’ll tuck you in and take a shower later,” he answered.

Jessica found the bubble bath and his words to be juvenile, but she thought it was sweet and let him clean her. Jessica also found herself with a sense of comfort she hadn’t had in quite some time. He lathered the bubbles on her breasts and gently scrubbed every inch of her body.

Later on he drained the tub and dried Jessica off with a marmalade towel and tucked her into his wide, cool bed. He planted a kiss on her forehead and one her mouth and Jessica found herself drifting into slumber.

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