High School Dates Ch. 11

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Going home for Christmas break.
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Part 11 of the 23 part series

Updated 11/09/2023
Created 03/24/2023
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m_storyman_x
m_storyman_x
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Authors note: I'm going to shift this chapter to Exhibition and voyeur. It'll come back to romance later, but this particular chapter is pretty heavy into that realm.

Chapter 15

I had to say, Jessica might be right. The best way to heal a broken heart might be lots of sex. If not, it was certainly one hell of a good distraction. It was no surprise that when mom had sex with me it was filled with emotion. What was a surprise was how much emotion I felt in Betsy when we had sex. It was definitely NOT just sex for her. She was truly sharing herself with me. I could see it in her eyes, hear it in her words and feel it in her actions each time we were intimately together. Last night was no exception, and if she kept pouring out her soul and love to me the way she did, it would be hard NOT to have that love I felt so many months ago, rekindle even though I was desperately trying to avoid it. I didn't want to be in love. I didn't want to be hurt like that again. Even with the amount of distraction, and the amount of caring I was getting from both mom and Betsy, there were times I struggled not to sit down and cry. I was clearly too emotional for my own good, and I had to learn to "toughen up!"

I'd promised Jessica that I'd be back the next morning. I had a few reservations, mostly that I kind of felt like I was using her, or maybe it was her using me? Either way, there wasn't any love. This was truly playful sex for enjoyments sake. I walked into the store and the little bell over the door ran as it was bumped. It didn't take long for me to find Mrs. Danning and Jessica. Jessica was putting some sexy little items on a hanger and Mrs. Danning was helping an older man select something, presumably for his wife.

"Hey hot stuff!" Jessica said cheerfully as she walked over to me, meeting me halfway between the door and the little rolling table she was working off of, several aisles away. She walked straight to me, wrapped both arms around my neck and pulled us together for a long wet, sexy kiss that had my cock already starting to harden by the time we broke the kiss. "Damn you feel good. I had to make myself come three times last night, just thinking about you."

I couldn't help but notice the guy turn his head and stare at us for a few seconds before he went back to listening to whatever her mom was telling him.

"Don't worry. I don't care who knows. He's gonna get an eyeful in a few minutes anyway. What?" She asked as I looked at her a little startled. "You worried about who might hear that your cock turns me on?"

"I'm not exactly used to it." I admitted.

"Well, get used to it. Apple doesn't fall far from the tree in my family."

"Huh?"

"Remember yesterday? Well, mom and I had a little chat last night. I pretty much hit the nail on the head. She loves showing off, I mean she really loves it. Yesterday was the first time she's ever let anyone touch her though."

"Oh."

"It explains why I'm kinda the same way."

"The same way?"

She giggled and whispered. "I love showing off. Who's idea do you think it was to do cheerleading practice that one time with no panties on? Flashing our stuff at all the football players? Ohhhhh. I still get chills just thinking about how it felt."

"You like showing off that much?"

"I do. One time I slipped into the shower with Tabitha's dad and masturbated in front of him while he watched."

"He just stood there and watched?"

She giggled. "Hell no. He stood there and watched while he jacked off and squirted his cum all over me. I always loved getting to stay over at a friend's house. I'd find ways to flash my stuff at their dads or brothers and then come back to the room and masturbate. One time I caught Gina's brother masturbating in his bedroom and stood outside his window watching through the gap in the curtain. I couldn't help it, I took all my clothes off and stood there in the backyard playing with myself when her dad walked out and saw me."

"What did you do?"

"What could I do? I stayed there and played with myself until he got a hardon and then I sucked his cock until he was ready to come and jacked him off all over my tits. I love watching a guy come almost as much as I love feeling him come in me. THAT is what I'm hoping you'll do today."

"Jessica. I can't just stand here and have sex with you."

"I don't expect you to. Mom and I have challenged each other to a little dare. You're going to the bakery with me, and mom is going to stay here and wear something you pick until we get back."

"Something I pick?"

"Uh huh. Anything red. Christmas you know."

"Wont people see her in it?"

"That's the whole idea. You can pick anything you want, as long as it's red. It can show as much or as little as you want, and she'll wear it until we get back. Most of the customers today will be men anyway, which really works out perfect since she loves showing off. SO how about it? Wanna pick something sexy for mom to wear?"

"I suppose I could."

"Good. The really sexy stuff is back here." She said, taking my hand and pulling me along the rack. She pulled one item off the rack and held it out. "Personally, I think she'd really look hot in this teddy."

"Oh damn. She'd really wear that?" I asked looking at the teddy she had pulled out. It was sheer, and I do mean see everything through it sheer, with a snap crotch. Yeah, she'd definitely look hot in this.

"She would if you asked her to. In fact, I think you should take it to her and ask her to put it on right now."

"She's with a customer."

"Uh huh. And by how he's looking at her every time she holds an outfit up to her body, he won't object to watching her put it on."

"What are you gonna be doing?"

"Watching. Don't worry, you'll get to see me naked soon enough."

"If that's what you want." I said with a shrug. I hadn't ever really been with anyone that loved showing off like this. For that matter, I wasn't sure how I felt about it, half expecting to end up having to flash my stuff too.

"It's the only way you're gonna get to see your Christmas surprise from her."

"Surprise? Like what?"

"Have to go ask her to put it on to find out."

I shrugged and headed down the aisle toward her, carrying the little see through outfit on the hanger.

"David! Good morning!" She said brightly, looking past the gentleman she was helping.

"Jessica asked if you'd model this for me."

She looked at the see through teddy and then at my face with a mixture of what I guessed was hesitation and apprehension. Then she nodded and stepped past the man to reach for the hanger. "I'd love to." She answered. She turned to the man she was helping. "This won't take long. Please, feel free to keep browsing."

"Alright." He said, moving a few feet away to look at the items hanging on the rack he was by.

"Well. this certainly is...does...oh yes, it does." She said with a look of determination. She lowered her voice to a whisper, hopefully that only I could hear. "Besides yesterday, this would definitely be the most exposed thing I've worn on the sales floor. I've modeled some like this, and even less, in changing rooms, but not out here." She said looking around. "But that was the dare, put on whatever you picked, right where I am when you ask."

I could see her hands tremble a little as she unbuttoned the first few buttons of her dress, undoing one button at a time down the front until she ran out of buttons at her waist. She reached up and slipped the dress off her shoulders and slid it down her arms and upper body. The guy turned to watch, staring with his mouth hanging open as she pushed the dress down. She had on a small blue lace bra and blue panties to match her dress. She stepped out of the dress and laid it on the rack next to her. She continued to stand there, knowing full well that the man was watching as well as I was, and reached behind her back. In moments the little blue lace bra was sliding down her arms, exposing her tits and perky, rock hard, nipples.

I could see her blushing slightly as she laid the bra on the rack and then moved her hands to her panties. She hesitated, her fingers toying with the waistband of her panties for several seconds and then began to slowly, very slowly pull them down. She turned her back to me, exposing her front to the man leaning on the rack staring, and continued to pull the panties down over her hips and full round butt. She bent over, standing straight legged as she bent, pushing her butt and her pussy lips out at me, my hardon straining against my pants t the sight. Lower and lower she went, pushing the panties down to her ankles, her butt pushing out more at me, her clearly wet pussy lips pushing out invitingly. Part of me wanted to just pull my now rock hard dick out and push it into her, but I just stood there and stared as she stepped out of the panties. She straightened and turned to face me. It took several seconds of her standing there, naked, before I realized what was different. She was shaved, where yesterday she was quite hairy between her legs.

She stepped toward me and reached for my hand. She pulled it to her crotch and pressed my fingers between her thighs, my fingers feeling her hot wet lips. She leaned closer, her hard nipples brushing my jacket as she whispered, "When you get back from the bakery, you can sit me on the counter by the register and lick me to your hearts content. I hope you do. I hope you make me come for you because I'm getting so damn turned on again. Maybe you'd even like to put this into me again after you make me come?" She said as she reached to my pants and rubbed my rock hard erection though my pants. "Would you like that? To make me come and then put this in me again like yesterday?"

"Oh damn yes." I mumbled, practically ready to pull my pants down right now and fuck her.

She straightened up and backed away. She grinned as she pulled the little red teddy off the hanger and then pulled it over her head. She slipped the see through material down her body and spread her legs to reach between them and snap the crotch. She was dressed, but you could clearly see, not only her rock hard nipples and puckered areola, but her now shaved pussy as well. I'd probably still be staring at her if Jessica hadn't pulled me gently from behind.

"Time for me to change." She said with a crooked little grin.

"Change into what?"

"What I'm wearing to the bakery." She said, pulling me by the hand to the checkout counter. "You didn't think that she was going to dare me to wear regular clothes, did you?" She stopped and turned to face me. She didn't have much on to start with. In fact, the ONLY thing she had on was the sweater dress and the knee length boots. She slipped the sweater dress up and off her body and laid it on the counter. Then she picked up her coat and slipped it on over her completely naked body. "Okay. I'm ready."

I looked at her, the front of her coat hanging open so her pussy was on display for me and shook my head in confusion. "I don't get it. You're wearing just that?"

"Uh huh. And just to make things more interesting, you get to tease me all the way there. The dare was to arrive at the bakery to pick up my order of cheesecake as close to orgasm as possible, and to make sure I orgasmed before I left the store."

"How are you going to do that?"

"Oh honey. That's the easy part." She said with a grin. "We're just going to stand over in the corner with me in front of you and you're going to slip your hands under my coat and play with my pussy until you make me climax."

"Seriously? You want me to make you come, in the store?"

"That was the dare. Think you're up to it?"

"Not like I've ever done anything like that before, but then, I hadn't ever had sex in public before Patty. You think you're up to it?" I asked honestly, looking at the parts of her body that were showing.

"Definitely! I've always wanted to do something like this but didn't have a guy I trusted to not go overboard. You won't go overboard, will you?"

"Overboard? As in?"

"Doing something like taking my coat off in the store or something like that. You can touch me, but how much my coat is open is all up to me."

"If that's what you want. Yeah. I'll agree to that."

In reply she grinned, and took my hand. I walked to the door with her, looking back to see her mom helping the guy that had been there when this all started, his eyes a lot more on her body than on what she was showing him. Though when I think about it, her body was exactly what she intended for him to look at.

The drive over to the bakery wasn't all that short. It was damn cold out and I pushed her coat apart enough to expose most of her body, her nipples sticking out rigidly, either from excitement, or from cold, or both. I sat on the bench seat next to her while she drove, my left hand between her thighs, teasing her wet pussy and her hard clit with the side of my pinky finger. We stopped at one intersection and had to wait for the light. There weren't too many cars around so I twisted around enough to lean down and suck on one of her nipples, drawing a gasp and moan from her.

"You keep that up and you're going to make me come before we get there."

"We wouldn't want to do that, would we?" I answered with grin, starting to really get turned on and into this whole crazy thing. "Can I ask you something?"

"Sure. Anything. I mean it doesn't get more personal than fucking."

"Did you talk to Mandy last night?"

She was silent for long seconds. "Yeah. I did."

"Did she put you up to this?"

"If you think she put me up to this silly dare, no. That was mom all the way."

"I kind of would like to know what it was that made her go to that party. Part of me wants to blame myself for having sex with my tutor that day and maybe this was her way of getting things even."

"You mean like her mom and dad?" She asked, looking at me. "yeah, I heard all about that."

"Yeah. I mean, that was crazy, what her mom did because of her dad fucking that black girl. I don't even remember her name."

"I've known Mandy for a long time. Her parents have an unusual relationship. One time she caught him perving on us girls out near the pool. I overheard her tell him he better get an eyeful now, because she'd return the favor one day of her choosing. The next time they had a dinner party, she was showing off her new bikini, which, according to Mandy, disintegrated in the water right in front of three of the husbands. She ended up completely naked in front of everyone, but instead of running off in embarrassment, which was what a normal person would do, she just calmly walked over to the ladder and climbed out and wrapped a towel around herself. The rest of the night she spent in just the towel, which apparently had a habit of slipping off much of the night."

"Weren't the other wives upset?"

"At first, until she explained why she was doing it. Then they said it was fine. I'm sure they all got some good sex when they got home."

"So, you don't think she was doing something like that to me?"

"I don't think so. She's so upset with what has happened. I don't think it was that at all. I think she just got in over her head at that party and had too much to drink. You can't blame yourself. You have done so much to help and protect her that I don't think she has the ability to intentionally cheat on you. Evan used to pimp her out. You know, swap girlfriends for sex with his friends. So, she didn't have many monogamous tendencies. But that night, the night of the sleepover, she confided in me that even though she promised us all a fuck with you, that she didn't want to. She changed her mind and didn't want to share you with anyone. I think that night changed something in her. For once she was watching someone she truly cared about, being touched by another woman, and I think it hurt. I don't think she'd willingly do that to you. Not after that night."

"Okay. I just wondered." I answered as we pulled off the street into a parking lot.

"Well, here we are. So, these are the rules. I have to get the cake. Then we can go to the corner of the store and you can make me climax. I have to hold the cheesecake, so I can't stop you from doing anything you want, but I'm going to ask that you please not expose me too much. Some is okay. but don't take my coat all the way off or anything. I like showing off, but only in glimpses. I don't think I could just strip down and walk down the street or anything."

"Okay. I'll try to keep it as if you were mine."

She turned and leaned to me. She kissed me on the lips and then smiled. "That might be the sweetest thing a guy has ever said. Thank you."

I nodded and we climbed from the car. Her coat was barely long enough to cover her butt, so anyone looking close would have to guess she had almost nothing on under the coat. We stood in line with three other customers, waiting to get our turn. I stood behind her, letting my fingers rub her butt under the back of her coat, coaxing the bottom edge up a little bit more as seconds passed, not because I was trying to flash her to anyone that might come in behind us, but because I was getting more turned on by the moment, which was making me a little bolder.

By the time we got to the counter I had one finger in her pussy, slowly teasing the tip in and out of her as she asked for her order. I pushed my finger in a little further and heard her stifle a moan as the person behind the counter went to get her order out of the cooler in the back. With no one in the store but us, and the clerk in the back, I pushed my finger in and out of her a little harder, pushing more of it into her depths. She was unable to stifle the moan that slipped out this time.

"Oh fuck you're so damn naughty." She whispered as I pushed my finger in and out as far as I could. I heard the door behind me open to let another customer in, so I quickly pulled my finger out of her and let her coat fall back in place, wondering how much the new person saw. I discreetly turned to look behind me and saw a woman in her middle forties or so, looking at me with a scowl. Must have seen more than I intended.

The clerk came back with her cheesecake, and she let the coat she had been holding closed slip, open as she dug in her purse for the money. I could see the clerk's eyes get as big as saucers as he realized just how much of her he was looking at. She handed him the money and he went to the register, Jessica leaving her coat hanging open while he did. He brought her change back and I could see the coat spread even further apart as she reached over the tall counter for her change. She stood putting the change in her purse for long seconds, letting him take a long look before she hung her purse on her shoulder, her motion pulling her coat far enough apart for a moment to easily show off one of her bare tits and all the way down to her equally bare pussy. She reached out and picked up the cake off the counter and turned away, making sure to keep the woman behind me from seeing she was naked under the coat. She walked over to the corner of the shop near where the bathroom was, and while the woman behind us started dealing with her request, stood in front of the plate glass window. I stepped over to her and slipped one hand around her. I spread the bottom of her coat enough to reach her pussy with my left hand, which also exposed almost all of her front to anyone outside the little shop.

"Oh fuck. Make me come." She whispered. "I wish I could fuck you right here."

"I was almost tempted to pull it out and fuck you while we were in line." I whispered back as I started to stroke her clit with one finger, rubbing up and down her wet pussy lips. "Just pull up the back of your coat and push my rock hard cock into you, sliding it in oh so slowly." I whispered as I moved my finger over and around her clit.

m_storyman_x
m_storyman_x
10,454 Followers