Cyber Sex
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Cyber School free porn video
My name is Hugh Bailey. I work at a large sporting goods store. We provide uniforms and jerseys to local teams as well as custom trophies, banners, and equipment. It is a competitive business so naturally, the company president encourages the staff to give back to the community. The company is very community minded in that regard.
My role is as a math tutor for the Catholic Welfare Mission high school students. It is impossible for me to reach most students in person because of the distances involved, so I tutor online. Most of it is helping students with their homework.
This volunteer work is rewarding in many ways. Mostly, it is feedback from students who say, "I finally get it!" or "I didn't think I was good at math until now," or "You encouraged me to take more math classes." Yet, there was another perk that is worth mentioning.
Whitney was struggling with Advanced Algebra in her junior year. She's a bright girl and easily teachable. I liked her attitude and found myself spending more and more time with her online. We got along very well, sometimes exchanging personal information.
Whitney had told me she was living at the Mission Children's home because her stepfather had abused her. No one knows where her mother is since she left the family a year ago. It was the classic dysfunctional family.
She wanted to know how old I was, if I was married, and what kind of job I had. Socializing wasn't a problem for me as long as it didn't get in the way of her studies, until one day that changed everything.
The tutoring session began as usual with quadratic equations and polynomials. Whitney suggested we take a break because she wanted to ask me a question.
"Mr. Bailey, I need some help on something. It's something I can't ask the Mission nuns."
"Sure, what's on your mind?" I asked.
"It's my boyfriend. We've been having sex, and I'm afraid of getting pregnant."
"Of course. You're too young to be a mother. Can't sex wait for just a little longer?"
"No, Mr. Bailey. If I don't have sex with him, he'll just go find another girlfriend. I like him and really, I like having sex with him."
"Then you need protection."
"I know and that's the problem. The nuns here will not permit any of us girls to take birth control pills."
"What's your boyfriend's name?"
"Justin."
"Well, have Justin wear condoms."
"Yeah, I know but he won't. He says wearing a condom is like eating a candy bar with the wrapper on."
"Hmmm, I'm beginning to see the problem. Do you know about the rhythm method of birth control?"
"No. Does it include visiting a doctor?"
"No," I told her. "It involves a calendar and a little math."
"How does it work?" she asked.
"It's all about planning ahead and good timing."
"That doesn't tell me much, Mr. Bailey."
"Okay, the idea is to avoid sex when you are most likely to get pregnant. Those are called your fertile days during the month."
"So I have to somehow figure out when I can get pregnant. I thought I could get pregnant any day."
"Well one reason you haven't gotten pregnant so far is that you lucked out, and didn't have unprotected sex on your fertile days."
"Tell me how to do it."
"Tomorrow, I'll send you a link to a site that gives you the details. It will tell you everything you need to know."
"Oh thanks, Mr. Bailey."
A few days after sending Whitney the information, she sent me a reply saying, "Thanks, but no thanks. It will never work."
At the next tutoring session, I asked why it couldn't work.
"Well, it's like this. Justin is a truck driver. I met him one day when he delivered a package to the Mission Home. We talked and he asked for my e-mail address. Anyway, I only see him when he is in the area. His schedule doesn't always match my monthly schedule."
"How old is Justin?"
"He's twenty-six."
"My god, Whitney, he's almost ten years older than you."
"Only nine, Mr. Bailey. Does it make a difference? I mean I like older guys. It's not like we're planning on getting married. We're just having fun."
"How did having sex with him go from a delivery man to being worried about getting pregnant?"
"Oh, he asked me for a picture. I sent him a picture of me in a bikini from last summer. He liked it and said I was sexy. I'll send you the picture and you can see if you agree."
"What then?"
"Oh, I don't remember. I think I asked for his picture. His was great. He wore a tight fitting swim suit. It showed a big bulge, you know, down there. I told him I liked it, and he was sexy too. That got us into sexting.
"Justin wanted a selfie of me topless. I'm proud of my breasts, so I sent it to him. I'll even send you one. He sent me his selfie without wearing swim trunks. He's got a great ass. Later, he wanted some nudes of me. I sent him a couple, and he sent me some of him with an erection. God he is big. He said he'd like to deliver something in my pussy. I said I'd like to suck his awesome wiener. I thought we were just playing around.
"Well, the next time he came to the Mission, he made sure I was there. It was right after school when he took me inside his delivery van, and we did it. Every time he is in the area, he stops by to see me, and we go in the back of his van for awhile. You can see why our schedules don't match."
"Okay, Whitney, it still can work. If he makes a delivery on one of your fertile days, let him know you are unavailable. Maybe you can give him a blow job to keep him happy."
Whitney agreed to see if Justin would go along with it. So she kept track of her monthly cycle for a few months, and things seemed to be working out fine. Oh, and she sent me her bikini and topless pictures. What I saw (which I've shared here) was a teenager that looked much older than seventeen with a mature body sent from heaven. Her tits are gorgeous.
Justin grumbled about not getting into her pussy, but having her suck his cock was acceptable, especially as Whitney learned to deep throat. Of course he always wanted her to swallow. He said it was extra sexy.
But good things have a shelf life. One week, it didn't work out as planned. It wasn't anyone's fault, but Whitney was in a panic.
"Mr. Bailey, I'm in trouble. He got me pregnant. I know I'm pregnant."
"Calm down, Whitney. How do you know your pregnant?"
"We had sex twice this week in the middle of my fertile time. I don't know why I did it. I shouldn't have, but it just happened."
"Here's what you do, Whitney. Go to the drug store and look for a product called 'Plan B, One Step'. It's an over the counter product. You don't need a prescription. Take the pill right away. Don't wait. The sooner you take it, the more effective it will be."
"What does it do."
"It's an emergency contraceptive pill. It keeps you from getting pregnant after having sperm inside you."
"Oh thank you, thank you, Mr. Bailey."
By some miracle, Whitney didn't get pregnant by the time she left the Mission Home. After high school graduation, she was asked to join the convent and become a nun. If not, she was pretty much on her own. I told her I had an extra bedroom, and she was welcome to stay with me until she found a job and a place of her own. In fact, I found her a job at our sporting goods store.
The first week together was a matter of organizing our schedules and making sure neither of us invaded the other's privacy. By the second week, we had it pretty much together, and made a doctor's appointment for a birth control prescription. By the third week, she was on the pill, and had a job as a checkout clerk.
I heard her moaning one night and stopped in her room to see what was wrong. Just as I knocked on her door, she stopped. "Anything wrong Whitney?"
"No, I'm okay. Just having a bad dream."
But the "bad dreams" continued on other nights until I peeked into the room to see her naked in bed masturbating. I'm afraid I got a little excited watching, and had to take care of myself in the next room. It was apparent to me that we were going to share the same bed soon. It was sooner than I had expected.
Two nights later she came into my bedroom crying. She rolled into bed next to me and said, "I'm scared, Mr. Bailey."
I put my arms around her, and realized she was totally naked. "What's wrong, sweetheart?"
"A guy at work gave me a ride home the other day. The thing is, he parked the car, unzipped his pants, and took out this long thick dick. He's a nice guy and has an amazingly cock. So when he pulled my head down, I didn't mind sucking it."
"Okay, then why are you scared? You've done that many times with Justin."
"He keeps asking for another blow job and if I don't do it, he says he'll tell the boss that I'm stealing money from the cash register. Mr. Bailey, I've never stole a thing in my life, but I know that's what he's doing. He takes things that people return, and sells them on eBay."
"Do you know his name?"
"Yeah, it's Tyronne."
"I'll take care of it babe. He's part time, and I'll make sure that now he gets some unemployment time."
"Oh thank you," and she rolled over to give me a kiss.
I thought Whitney would leave but instead her hand found my crotch and, my pulsing erection. She didn't ask permission when her lips circled my cock. I didn't object when the girl took all eight inches of me down her throat. I burst loads of cum into her mouth much too fast. She swallowed and smiled saying, "Gosh Mr. Bailey, that was fast." It was also just the beginning.
Two nights later, she came back and pulled me on top of her. "I want to show you what Justin and I did on days we couldn't do it like we wanted." Whitney had my cock between her two luscious tits and gave me the best tit fuck I guy could hope for. This time, I didn't embarrass myself like earlier, and didn't cum right away. It still ended with multiple shots having the force of a submachine gun. Some of it hit her forehead, eyes, and mouth. She simply scooped it off her face and licked it off her fingers. "You know, Mr. Bailey," she purred, "yours tastes so much better than Tyronne's." I took that as a compliment.
"Look, Whitney, it's time you called me Hugh," and from then on, that's what she called me.
The next time she joined me in bed, she wanted to thank me for helping her with the Tyronne problem. It was a pretext for what she really wanted. Whitney needed sex. "Would you help me get off tonight, Hugh? Doing it myself isn't working. I need some love down there."
She spread her legs and gently lowered my face between her thighs. I gorged on her pussy like a wolf devouring it's prey. One, then two of my fingers slid into her juicy cunt. Her moans got louder and louder. Whitney began squealing like a crying piglet, then let out a scream. Her hips gyrated, and her orgasms came with rush of fluids that painted my tongue. "Fuck me, please fuck me. I need it so bad, so bad. I haven't had it since I left the Mission. Come on, squirt your hot cum in me. Please, please," she begged.
My cock disappeared in her pussy with one push. Dozens more push and pulls in her tight pussy followed, then much too soon, my grunts and groans accompanied a series of cum shots fired balls deep into her young cunt. I was finished; she wasn't.
The moment I pulled out with a cock creamed with cum, Whitney pushed it back in, turned on top of me, then rode me for another round. If it wasn't for her dirty talk, "Fuck my cunt. Slam that dick of yours deeper. Bang me harder. Make my sloppy pussy cum," I could never have stayed hard long enough to cum for second time.
The girl had an insatiable appetite for sex. In the days and weeks that followed, Whitney and I slept together having sex most nights. She was adventurous and playful in bed, becoming my bedtime tutor. We tried everything, even sex during her period. I didn't mind, and she said it made her feel sexy and more like a woman.
There was a night she came into the bedroom smiling with my razor and shaving cream, saying "Surprise!" Then she shaved me clean. Her idea was for me to straddle her face, hanging my hairless balls over her lips so she could play with them. She kissed, licked and sucked them until I couldn't stand it any longer, sticking my cock in those sweet smiling lips. Needless to say, she got a mouthful.
The best of the best was when she was on top. I could see those magnificent tits flopping, her sensuous facial expressions, her eyes rolling with pleasure, and the way she quivered with each orgasm. She would plead for me to last longer and longer. "Please Mr. Bailey, please Hugh, wait a little longer. Please don't cum yet. I'm close. I'm really really close. I'm going to cum. Fuck, fuck, fuck, I'm cumming." At that, she had a tremor of a climax, and I exploded inside her.
Sometimes we made it an all nighter. We'd play with each other's sensual places and dare the other not to cum. I got very good at holding back. This extended our pleasure time, and we could fuck several times each night.
Over time, Whitney was doing very well at the sporting goods store. After six months, she was named the assistant sales manager. The rumor at the store was that she was promoted by sleeping with the owner. Knowing Whitney as I did, I doubted that was her motivation, although she was spending more and more time in the owner's office. My best guess is that he was getting her signature blow job and tit fuck. After all, she liked older men.
Sometimes her new responsibilities required her to work the night shift which made neither of us happy. It also allowed her to meet new people, one of which was Miles, the owner's son. Miles and her got along very well, too well. I, of course, had no say in the matter when she didn't come home at night.
Whitney said she was in love and wanted to move in with Miles. I could only encourage her to follow her heart. A month later she moved in with Miles, and they were married in a year. She had done alright for herself in a short time.
Whitney didn't completely desert me. When Miles was away on business trips, she'd stay the night with me for old time sake. Whitney said, "Okay, I married the guy but that doesn't mean I have to be alone when he's away."
Once while she was pregnant, she asked to see me at home. She told me that Miles refused to have sex with her now that she is having a baby. "I'm with his kid, but I still get horny at times," she said. "I need it just like always."
I fucked her from time to time right up to the end. God, those tits got so big, it was like two huge milk jugs about to burst.
Whitney eventually left Miles and the sporting goods store. She ran off with Justin with whom she had secretly kept in contact. Now I've lost track of her. It goes without saying that I miss her, those big tits and our playful nights together.
Alessandra
- 10.01.2021
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