Jake's Odyssee Ch. 02

Teddy Intro (MAR 2014)

Teddy was born in Brazil in October 1995. Her father left the family when she was five and didn't remember him very well.

Her mother dated a lot of men throughout her childhood. They would take her and her mother out to eat, maybe to a theme park occasionally, or just to go shopping. Her mother's boyfriends always paid for them wherever they went and would sometimes just bring gifts when they came over, but they never dated long enough for Teddy to get attached to any of them.

Teddy began dating after she turned 18. She had brunette hair, brown eyes, and tanned skin. She was about a C-cup size, and had a thick Brazilian booty.

When she was at a park with her friends after school one day (she was still a senior), she ran into a boy a who had already graduated named Diego.

He was 20, had dark curly hair, was about 5'9" and had blue eyes. Teddy had been crushing over him ever since they met at the beginning of the year. He talked smoothly and calmly and had a deep and commanding voice as well.

When she started to talk to him, she realized he didn't even remember her from when they first met, but she was still so attracted to him and wanted to get to know him more, so she kept trying to talk to him when she could without being overbearing. Eventually, he agreed to hang out with her. He never seemed to care much, but she did.

Eventually, they started to date officially. Diego had a beautiful and long 7-inch cock which, after she lost her virginity to him, he started to teach her what to do and how to do it. She crazed over it.

Most of the time, he would fuck her pussy or her face, but almost every time they had sex, he would make sure that she swallowed every drop of cum he excreted. She didn't particularly enjoy it, but she did it for him every time.

About the same time her and Diego started dating, her mother met Jonathon. Teddy never got to know him very well, but she always felt like he looked at her a little to long for comfort.

About a month later, her mother said that her and Jonathon were going to go on a trip for the weekend and would be back Sunday night. Teddy was in her PJs for the night, a big t-shirt that went almost to her knees, with light-blue panties underneath.

Jonathon pulled into the driveway, came inside without knocking, and called into the house for her mother. "I'm almost ready, just grabbing the last couple things, be down in a minute!" she called back.

Jonathon saw Teddy, who had just walked out of the kitchen to see who was at the door. "Hey, Teddy bear!" He said, smiling at her.

"Hi," she said back.

"Hope you're doing ok, here I got ya something," he gave her a box. This was what most of her mother's boyfriend's gifts were usually in, so she wasn't surprised, and took the box quietly.

"Thank you," she said to him.

"You're welcome sweetie, have any plans for the weekend without us here?" he said to her and winked. She didn't really like him very much, but she figured he wouldn't stay with her mom for long anyways so she giggled and smiled back at him as she typically would do.

"No, not really. I'll probably just watch some TV and maybe go out to the mall with Diego." He nodded at her.

"Well, if you want, your mom wouldn't know if he came over and stayed the night over the weekend. I'm sure he could think of some more things to do if you ask him." He winked again, and she shuddered involuntarily.

Teddy heard her mom call out again and heard her footsteps as she descended the stairway to the front door. "Alright, I've got everything packed, I'll put these in the car and come back to say bye to you Teddy just give me one second."

"Okay mom," Teddy called back. Jonathon turned and watched until the front door closed again.

"Well, I'll miss you Teddy bear," and wrapped his arms around her and hugged her tightly. She didn't like hugs from her mom's boyfriends very much, but again, was something she had to deal with on a pretty normal basis growing up.

Her mom always got mad and yelled at her whenever she tried to move away or didn't hug back. It was probably her mom projecting anger that her boyfriends would express to her in private.

She put her smaller arms around his large back and turned her head to the side so her face wasn't smashed into his wide chest.

As he continued to lightly squeeze her body close to his, he said, "I have my number with a phone in the box I gave you, if you guys do anything I want you to send me a picture or video from it. If you don't I'll tell your mom you stole it from me."

She tried to move away but he held her tight. Then, he moved his large, rough hands down, got them under her shirt, guided them up her thighs, and squeezed her bare ass that was only barely covered by her panties. "I also have friends that know the address so don't tell your mom anything." Her ass cheeks jiggled as he let go of them and her shirt fell back down, just before her mom came back inside.

He let go slightly, kissed her forehead, and stepped back as her mom came up to her. A tear was forming in Teddy's eyes after going through the shock of what just happened.

Her mom hugged her, said "Now you be good this weekend, okay? No parties or boys over."

Teddy nodded her head as they hugged. Her mom let go and tilted Teddy's head towards her and saw the tear. "Oh my god sweetie what's wrong?"

Jonathon had his arms crossed. "She said she was just really sad to see us go for the whole weekend." Her mother looked back at her.

"Is that true hun?" Teddy thought of saying something but remembered what he said. 'I also have friends that know the address so don't tell your mom anything.'

She just nodded her head in defeat and felt more tears coming.

"Oh, I'm so sorry." She hugged her again. "We will be back as soon as possible; I would cancel it if we could get it refunded but all of the money is already spent." She said, attempting to console her.

After a few more minutes, Teddy's mom and Jonathon left the house and drove away. She opened the box, inside it she saw a smartphone, and a sticky note, with his number on it. She felt like throwing up.

After a long night of crying and trying to deal with what happened, Teddy turned on the phone, set it up, and connected it to the internet. She added Diego, her mom, and reluctantly Jonathon to her contacts.

She messaged Diego and her mom, telling them that was her new number. She did have a phone before, but it was a flip phone, she never had a smartphone before.

Not five minutes after, she got a message back, but it was from Jonathon. "Hey Teddy bear. Just wanted to make sure you have my number, your mom told me she got a message from you. Don't forget."

Any amount of recuperating she thought she had was all gone again. She hated him.

She got another message alert, this time from Diego. "Hey. home alone?" She just wanted her mind off things and thought he would be a good distraction. Part of her wanted to hide away forever, but she needed some distraction.

"Hi baby! Yes, I am, mom left yesterday."

About 10 minutes later, she got a message back from him. "On my way." Diego usually didn't ask; it was always what was going to happen. She was always head over heels for him, so she didn't mind it. She immediately put her makeup on and got dressed in her short shorts and tank top.

She waited for over an hour until she heard Diego's truck pull into her driveway. He knocked, and then opened the door.

"Hi baby!" Teddy came up and gave Diego a big hug. "Hey," He hugged her back. One of his hands went to her ass and she flinched for a second and then stopped herself.

"You okay..?" He asked.

"Yeah, I'm alright. I'm just happy you're here."

He smiled in response. "Let's go watch a movie in your room," he said as he let go of her.

"Okay!" And they went upstairs to Teddy's room. It was pretty small and had a lot of pink and purple girly decorations all throughout, including the blankets and pillows on her bed. She hopped onto it and grabbed the TV remote to try to find something to watch, as Diego came and sat beside her. He took off his shoes and kicked his feet up on her bed, putting his arm around her.

She finally found something, put her remote to her side, and laid down with him. They both wrapped their arms around each other and started making out.

Eventually, their hands coursed through each other's hair, and then to their bodies. Diego kissed and nibbled on her neck, and she gasped lightly in response.

His hand started pulling up her shirt, and she immediately took the whole thing off. She was already so wet and horny she didn't mind skipping a few steps.

His face moved down to her chest, and she closed her eyes as she felt his hands put light pressure around her breast, and then felt static throughout her body as his tongue stroked her nipple. She bit her lip, feeling his tongue rotate around it and his lips periodically close on it, sucking or lightly nibbling on it whenever he did.

After a few minutes of him playing with her, she couldn't take it anymore. "Baby fuck me," she whispered to him.

This brought him back up to her face and they passionately made out some more. "It's your turn now, then we will," he whispered back, and then she heard his zipper. She always knew this was the routine, but he made her so horny, she couldn't stand waiting longer, but that was Diego. A tease.

She sat up on the bed, as he continued to undo his pants. She never said no, so he knew she would obey without question. He grabbed his waistband and pulled his pants and drawers down, revealing his half-erect circumcised cock she had grown familiar with.

He always kept himself well groomed and washed, never any real negatives about giving him head except that it meant it wasn't fucking her yet.

She positioned her body between his legs, laid down on her stomach (because she knew it wouldn't be a short amount of time) and licked her lips. She brushed back her brunette hair, looked at Diego briefly with her big brown puppy dog eyes, and directed her attention back to his large member that was inches from her face.

It was pointing down, laying over his huge balls, like a resting, dormant snake. A snake she lusted over. His whole package looked like it could have been meant for a 7-foot tall, muscled man, but it was his.

She reached her right hand up, and softly wrapped her small fingers around his shaft, and started to move it up and down. She looked up and saw him biting his lip in anticipation, watching her every move. She smiled. This was one of the few times she felt she had power over him, if only temporarily. This was her penis now; she could care for it however she wanted.

She gave a small lick on the underside of the shaft, looking in his eyes as she did. She felt his cock flex strongly, and noticed it was getting harder very fast. She cupped her left hand on his big balls and played with them as she continued to lick around his cock.

She heard him breathing harder, as she moved to the head. She rotated her tongue around his head like an ice cream cone that you don't want to drip.

Finally, she put her lips on all sides of the head, sucked out the precum he had already pushed out naturally, and slowly pushed her head down, hearing him groan and filling her small mouth with his large, rock hard dick.

He reached the back of her throat fairly quickly, but his cock was the only one she had known, so she knew how to relax her throat and keep it under control.

She sucked his cock for at least another five minutes, with him grabbing her hair and shoving her head into his crotch, making her have to pull up for air.

She released her mouth and looked up at him, her face wet and slobbery, her eyes slightly red from choking. She was trying to catch her breath and also trying to control herself, she was so wet and ready for him.

She kept revving his cock with her hand, and asked him "do you want to fuck me now?"

He nodded, got up, and she laid onto her back on the bed, pulling off her short shorts, that were probably ruined now.

She watched him get up to his knees and now position his body between her legs, his cock still standing out erect and prominent from his body.

From his perspective, he saw all of Teddy's naturally-tanned body laying fully nude, waiting for him. Her smooth and hairless legs, slightly thickened thighs, her beautiful soft and wet pussy between them. Her wide hips but thin waist, supple breasts, and her beautiful face looking up at him, those eyes just begging him to fuck her already.

Diego laid his body down to her level, so that his cock was closer to her lower regions.

All of a sudden, she started to feel a large, warm, head pressing against the lips of her vagina. She was soaking wet at this point, so it didn't take long for it to push in.

She felt his head enter, and then she felt her body tingle all over as inches of his hard, thick shaft continued to push further inside.

Her eyes were closed while she was focusing on the feeling, then he pushed the rest of his length in. She gasped lightly, and looked up into his eyes.

She was so wet from all of the teasing that now his cock was soaked from that final push in. He pulled out and pushed in. They started to make out, she grabbed the hair on the back of his head, pulling him closer to her.

His thrusts started getting more of a steady pace, and she started to lightly moan while they continued to kiss passionately, her tits starting to jiggle slightly each time he pushed all the way inside her.

After a few more moments, Diego stopped kissing her, and moved down to her neck, nibbling and kissing it, while rubbing her nipples and squeezing her breasts as he fucked her. Teddy closed her eyes, bit her lip, and started to moan a little louder.

Now they were fucking at a faster pace, her tits jiggling, and the bed squeaking every once in a while.

She felt his hand drift from her breast, and his fingers traced her body down her stomach...he slowed his thrusts slightly as his fingers found their way down between her legs, and onto her clit.

She grabbed onto his bare back as she started really moaning now, and his thrusts got harder and harder as he found his rhythm with everything that was happening.

The bed squeaked on every thrust now, and he stayed at a fast pace. She started getting closer and closer to climaxing, still grabbing against his back, holding on as he rocked her world.

Nothing else in the world mattered at that moment, all she was feeling was that exciting and invigorating build-up. Meanwhile, his cock was revving up inside her, rock hard and enjoying the ecstasy of the warm and moist cushiony walls of her pussy.

They both felt their bodies get warmer, increasing their pace together. Teddy was first. Her nails scratched along his back as she released a final long moan, her leg lightly twitching in pleasure as she came over his dick.

He continued to fuck her harder, until he started feeling himself get to his last few strokes. He got faster and faster, then quickly stopped, held it in for a second, and pulled out. Teddy knew what to do, they had done this enough times now.

Teddy sat up, positioning his cock right in front of her beautiful face. She looked up at him, as he was jacking his cock, about to explode. She opened her mouth, stuck out her big tongue, and let him grab the hair on the back of her head, and pressed his cock on her tongue.

Then he started pushing into the back of her throat and she closed her lips around him. Now she relaxed her throat and let him fuck her just about as hard as he wanted to.

But usually at this point it wasn't for long. "Oh, oh, oh, ohhhuuuuuuuhhhhhhhh!" His meat was lodged all the way to the back of her throat, balls deep into her face, as he deposited several thick loads of cum directly into her stomach.

Her eyes started to water and she felt like she was really needing to breathe, but she held it out for him because she knew it made him happy. She felt each thick jet of cum coating her throat as she swallowed it all in succession. After a hand full of pulses and swallows, he let go of his grip on her hair, and she instantly pulled back to catch her breath.

Then she grabbed his cock and licked and sucked on it for a little longer to make sure she cleaned him up good and swallowed any leftover cum.

They laid in bed naked together for a couple minutes, and then went to take a shower together.

Diego started getting dressed and getting his stuff together. Then Teddy remembered Jonathon. She didn't want to do what he said, but she also didn't want anything bad to happen to her, or to get in any trouble from her mother if he lied and said something else to her.

"Baby..I have a question.." She said.

"Yeah, what's up?" Diego asked.

"Do you think..do you think I could like, take a picture of myself sucking your cock? I just want something I can look at later tonight if you aren't here.."

Diego looked really confused for a minute because he had never heard her ask for anything like this before. "Really? Like..right now?" He asked.

"Yeah..I just want to have it now so I don't forget later.." She said.

"Okay I guess, I mean I don't care, if that's what you want." Teddy pulled her phone out as Diego pulled his shorts back down, showing his still long but now soft cock.

She sucked his cock long enough for it to get at least semi-hard, and then angled the camera at herself, with her jaw wide open and Diego's schlong filling up her mouth.

She took a picture, and set the phone down. "Ok, thank you baby." She said, licking her lips.

"You're welcome, I've got to run though, I'll message you later." He grabbed his keys and phone, gave her a kiss, and left.

A few hours later, reality hit Teddy again, along with a good heavy dose of depression. Again, she didn't want anything bad to happen to her or her mom.

So, with tears starting to form again, she pulled up her messages with Jonathon, and clicked attach media. She found the picture with her mouth stretched out and filled with half of Diego's 7-inch cock, attached, and click send in an instant to get it over with like ripping off a band-aid.

She instantly started bawling and screamed into her pillow. Her phone vibrated. She looked at it.

"Good girl. Lucky guy. ;)" Teddy screamed into the air and threw her phone at the wall.

The next week, Teddy's mom told her that her and Jonathon had broken up. She was relieved, but still disgusted to know he had that picture still.

She didn't bring it up with her mom because she knew her mom would confront him and then the threats he promised could come true. She kept quiet about it and let it be, as much as she didn't want to.

Meanwhile, Jonathon was jacking off while looking at the picture Teddy sent, along with all of the pictures of her he had taken without her knowing.

Every time Teddy and Diego hung out, he seemed to always be on his phone. "Hey can we do something? I always feel like you're glued to your phone nowadays..." She said.

"Babe, you should make an instagram." He told her, ignoring her suggestion.

"What's instagram?" She asked.

"You post pictures on it, and people from around the world can like it and comment and talk to you. I think you can even make money on it if you're pretty or funny enough." He said, showing her his phone, which showed a ton of pictures of memes and models all over it.

"Do you think I'm pretty enough baby?" She said, nudging herself closer to him.

Diego shrugged. She looked at him shocked, "you asshole!" She said, but she didn't want to seem like a bitch and aggravate him, so she smiled and chuckled, and playfully hit his arm, even though it did hurt her feelings.