Henry excused himself from his family after dinner and retired to his bedroom. He said he was tired after a long, hot day cleaning pools and doing odd jobs around the neighborhood. But he just wanted to be alone.
The day had started out like many others for the eighteen-year-old. He had scheduled a lawn mowing for the Osborns and then a pool cleaning for Mrs. Haas. It was not necessarily his favorite kind of work, but it bought gas and wasn't difficult. He had wished he could get a regular job instead of what he saw as kid work--that is, he had wished that until today.
The lawn project went fine. It was the pool cleaning that had made his day.
First off, Mrs. Haas, recently widowed, was gorgeous and stacked, and she happened to be lying next to the pool in a skimpy two-piece. Those big tits of hers had tantalized him before, but today they were especially tempting.
Then, out of the blue, she asked Henry to sit and chat with her for a while. She was obviously lonely and even said so, But when Henry tried to console her, she broke into tears. He clumsily tried to comfort her with a hug, and that's when the day got brighter. The next thing he knew he was kissing her and her big boobs which was a prelude to her taking him into her bedroom and erasing the virgin designation from his resume'. She had even given him a blowjob before they fucked. And she indicated that as special as today was, there might be similar days in the future.
Henry removed the pair of silky panties he later stole from her bedroom as a souvenir. They were a used pair that had been discarded on the bedroom floor. All the better. He put them to his nose and inhaled the earthy perfumed scent of Jodi Haas. Instantly his cock became rigid.
For the rest of the day, he couldn't wait to get to his bedroom and beat off to the memory of that event. And now he was behind the locked door to his bedroom with a raging boner. Even though his door was festooned on the outside with warning signs to keep siblings and parents at bay, he didn't want to take the chance of his mother barging in unannounced while he had his cock wrapped in his neighbor's thong panties.
'Jesus, what a body!' he thought to himself. 'Mrs. Haas is way better than I imagined. Despite being in her mid to late thirties, she was trim and fit--except for those big tits that he had kissed and sucked. Her bra said 36D, but when he held it, even those huge cups seemed too small for those magnificent hooters. And then they were capped with huge nipples and areolae. He hadn't been able to get his lips around the whole nipple! Jesus, what a turn-on!
He was now sitting on the bed with a pillow for support and his cock already leaking pre-cum. Mrs. Haas' lavender panties were wrapped around his thick shaft and as nice as that felt, it was nothing compared to the velvety feel of her cunt. Jesus, she had a beautiful pussy and he had actually fucked it. The mental image of his cock entering her cunt was nearly too much. And she had commented on how big his cock was. The vision of his plum-sized cock-head slipping between her labia and entering her pussy was cemented in his brain, and he prayed he would never forget it. Hers was the first pussy he had ever fucked or even come close to fucking. What a fucking day!
"Oh my god, Henry--your cock is even bigger than my late husband's!" she had told him when she first saw it. Wow! And she actually sucked him off and swallowed his cum. A blowjob was until then only a thing of his fantasies. So as of today, he was no longer a virgin and had received a blowjob. There would be no bragging about it though-- as much as he'd like to boast to his friends. This had to remain a secret or it would never happen again. She had reminded him of that several times.
"Please, God. Let me fuck her again and I'll promise to be good for the rest of my life," he spoke out loud to no one.
Just then his reverie was interrupted by a knock on his bedroom door.
"Henry, what are you doing in there? You just disappeared all of a sudden."
"Nothing, Mom. I'm just taking a short nap. I didn't sleep well last night and I'm worn out." The panties were quickly discarded and his shorts pulled up just in case. His mother's voice erased his erection in a heartbeat.
"Ok, but don't sleep too long or you won't sleep well tonight."
"No worries, Mom. I'm just going to read in here. Thanks. I'll see you in the morning."
At the sound of her disappearing footsteps, the panties reemerged and were once again wrapped around his rigid penis and sliding up and down his thick shaft. Henry figured that if he masturbated enough, he could learn to control his orgasms so he wouldn't cum so fast the next time he screwed Mrs. Haas. He figured he probably couldn't always count on a blowjob to make him last longer. But then the thought of her full lips stretched around his cock was all it took and suddenly Henry was spilling his seed all over his fist and those wonderful panties. Thankfully he had remembered to grab a roll of paper towels. He was going to need it. God, he was so horny.
He wasn't scheduled to clean Mrs. Haas' pool for another two weeks, and the time dragged incessantly. Years later, the day finally arrived and Henry wore a clean pair of shorts, a haircut, a perpetual hard-on, and even a shave. He wanted to look his most desirable for the job at hand.
He had been watching the house next door carefully all morning. The last thing he wanted was to arrive when no one was home and ruin his chances. But around noon, he saw a car pull into the driveway and into the garage. At long last, she was home.
Henry waited a few minutes before yelling to his mother that he'd be gone for the afternoon doing jobs, and then headed next door. Rather than go directly into the backyard and start cleaning, he knocked on the front door. He heard footsteps and then the door opened and there she was.
She was wearing a pair of jogging shorts and a nylon top with a broad smile to go with it. Henry was hoping for no bra and his prayers were answered. Those big boobs jutted proudly, straining against her top and gravity.
"Oh, hi, Henry. What's up?"
"Pool cleaning day, Mrs. Haas. And anything else you might need." Like a hard cock from a horny teenager.
"Oh, that's right. Well, you know where everything is. I'll leave you to it. Let me know if you need anything else. I'm just putting away some groceries in the kitchen and doing a little straightening up. The house is a mess."
Henry felt rejected. He had hoped for an open-arms welcome with passionate kisses and a romp in the bedroom with his big pole buried in her. Instead, he was dragging a twelve-foot aluminum pole around her pool collecting leaves and other debris. This was not what he had in mind or had been praying for during the last two weeks.
Henry continued to work in the yard and clean the pool, but his thoughts were elsewhere. When he was done he put the tools away and was preparing to leave through the back gate, his face a picture of disappointment. Just then the atrium door opened and Mrs. Haas stepped out.
“Henry would you come in for a few minutes I think we need to talk.“
Henry trudged to the door, expecting to get a "dear Henry" lecture, or at least the equivalent of one. As he was cleaning the pool he realized that his dreams were too good to be true. He'd been busy practicing with her panties for two weeks and was confident he would be a new and improved, longer-lasting version, but it looked like it was all for naught.
He gave her a shy smile as he approached the door. His six-foot frame towered over her. "Hi Jodi...umm...Mrs. Haas. What's up?" He was doing his best to act casual as he steeled himself for the bad news.
"It's still Jodi, ok? No more Mrs. Haas. Come on in, Honey. I've been doing some thinking. Have a seat. Would you like something to drink? Water? Iced tea?"
He accepted her offer and when she set the tea in front of him, she sat down across from him at the kitchen table.
"Henry, I'm guessing you were hoping for a different kind of reception from me when you showed up. I could tell you were disappointed. You were probably hoping I'd open the door in a negligee or even naked. I do know something about the way men think." She smiled and reached across the table and held his hand in her two hands.
"Well, maybe, just a little like that. Honestly, you are all I've thought about since the last time I was here, Jodi. And, I guess I was hoping for something similar. I'm sorry if that sounds selfish. I know that you are lonely and I probably took advantage of that before. Now, I'm feeling sort of ashamed."
"Oh, Honey, please don't feel that way. If anyone was taken advantage of, it was you. I needed a man and you were there. Please don't feel bad about it. You were wonderful. And I loved what we did. Of course, I've had second thoughts about it, but I want you to know that I've thought about you as well. And, well, I just need to be honest with you."
'Here it comes, the Dear John part.'
"Henry, I'm an old lady compared to you and the girls you should be chasing. But I do have needs and quite frankly, I don't want to get involved in messy affairs with married men or other's who just want to bang me. So, here is what I'm proposing: I would love to extend our little experiment, but only under certain conditions. You'd have to agree to all of them and that may not be easy."
Henry's cock hardened immediately. He couldn't believe his ears. She still wanted him.
Whatever you say, Mrs...Jodi. I'll do anything for you. Just name it."
"Well, first this has to be by mutual agreement--always. Anytime either of us says no, no means no.
"Of course!"
Secondly, you'll be going off to college in the fall. By then, things may have changed, but we will tentatively plan to end it then if, in fact, it lasts that long. We can reassess, of course, but either one of us may have found someone else, so I'm calling a cease-fire in advance. Once you leave for school, no more talk of this unless we both agree to continue.
"Sure." Henry didn't want any deadlines or ultimatums, but at this point, he'd agree to waterboarding if need be.
Finally, no one can know about this. No one! I'll tell your mom that I'm hoping you can do some of the chores that James used to do, and that won't be a lie, will it? I don't want to sound like this is sex for hire, but I'll pay you to do other chores as well...mowing, painting, things like that. But if I hear even a hint of a rumor about any of this, it all stops. Understand? No locker room bragging about how you are shagging Mrs. Haas."
"Oh, no worries, Jodi. I swear. Lips sealed. I think too much of you to tell anyone about us. And I'm not like that anyway."
"Look, Honey. This changes everything. You are a man now and with that comes responsibilities. I think I can teach you a thing or two if you will accept these conditions. But one other thing, Henry...."
"Sure, anything. Name it."
"This will not be a romantic relationship per se between us. I know you have a crush on me, but mostly you have a crush on my body and having sex with me. You need to treat me with respect, but understand that this is about needs for both of us, and while I hope love is involved, we will be lovers, but with no hope for more than that. I'm old enough to be your mother. But at the same time, I know how these things can evolve. We need to keep it in perspective. I love the fact that you are becoming a man but already have a man's body. And you are getting the benefit of a fully formed lady who will teach you what I can about how to please a woman in every way. One of the keys to happiness that James and I shared was mutual respect in and out of the bedroom."
"Thank you so much for all of this. I will be a great student, I promise. You are already making a difference in my life."
"Just one final thing."
"Anything, just name it."
"You should probably give my panties back for now. We don't need your mother discovering them, do we? I don't think you'll need them anymore, either."
"I'm sorry about that. I just wanted something to remember you by. That was stupid. I'll get them back to you."
"Ok, no worries. How about this. Bring them over when you are done with your chores for the other neighbors today. I'll try to give you a warmer welcome at the same time. Truth be told, I've been horny all week waiting for you to clean the pool." Jodi grabbed a key from a kitchen drawer. "Here's a key to the back door. When you come in just give a shout so I don't think it's a burglar. As long as I'm expecting you, no need to knock."
They both stood, and Jodi kissed him. It started as a motherly peck but once their lips touched, both mouths opened and found one another's tongue. Jodi felt a swelling in her partner. His six-foot frame put his penis in her 5'5" midsection.
"Somebody's getting excited. I can hardly wait as well, but I'll see you later, Henry. Right now I'm going to take a nice, hot, bath."
Henry imagined those big tits floating in a bubble bath as he mowed the Wilsons' lawn down the street. When he was done, he raced home and took a quick shower.
"What's the hurry?" his mom asked as he quickly dressed and was heading for the door. "By the way, you're on your own tonight. Your father and I are going out to dinner. There's leftover lasagna and salad in the fridge. So where are you heading in such a rush?"
"No rush. Just dropping by Mrs. Haas' house next door. She said she had more work lined up for me and I said I'd drop by later today to see what she needs. More work means more college money. Sound like she needs a guy for some heavy lifting and stuff. See you later. I'll be fine for dinner. Enjoy your evening out."