Jonathon And Jackie Naked In SchoolChapter 2 Jackie
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Jonathon Learns Some Life Lessons free porn video
He stood there holding his clothes as she bid him farewell. “But what about…”
“Oh yea, come back tomorrow night and we’ll take that off of you.”
He blanched at the thought. He wondered furiously how he ended up in this situation. He had met her at the club, his first time there. She was drop-dead gorgeous and he thought he had really lucked out. They had a few drinks, danced and as the evening ended, she talked him into going home with her. It hadn’t taken a lot, even though she said she was on the kinky side. She made it sound like he would be less a man if he didn’t go with her.
That's how he ended up with a sore ass and his cock in a pink plastic contraption with a built-in lock. When she mentioned pegging, he should have admitted he didn’t know what it was. Instead, he tried to bluff his way through it and that's how he ended up with a dildo up his ass. She went to her bedroom after they spent an hour naked on her couch teasing each other until he didn't even think he could back down.
She stepped into her bedroom for a minute and when she came out, she wore a harness with a cock hanging from it. He was shocked, but still really didn’t understand the concept. She gave him a lesson and then even teased him as he came from getting fucked in the butt once the pain lessened. In the afterglow, how she talked him into the cock cage still didn’t make sense, right up until she clicked it closed and then tried to give him a blow job which made his cock start to harden until it hurt.
She never laughed at him, she just kept things going until she was done with him. He ate her pussy longer and more forceful than he had ever done it before. It was partly because of the implied promise of getting unlocked but as he brought her to orgasm after orgasm, he actually felt a little proud of himself. He did other things he never considered sexual, like licking her ass, her armpits, and sucking her toes. He thought she might have been laughing at the second orgasm of his which it dribbled out of the hole at the tip of the pink plastic cage. But instead of laughing, she caught it on her finger and wiped it on his lips. He could still taste it.
When even he realized they were done, she made a show of trying to find the key and failed. He dressed, the cage made a noticeable bulge in his pants as she promised to find the key or she would get the spare key from the girlfriend who had given it to her to play with. He went home not a happy man.
He slept badly, every time he turned over, the cage was uncomfortable and in the morning, he had a full bladder and it really made his cock ache. He tried to get it off, but it was locked tight and the ring around his nuts might be pink but was coated steel. He felt weird as he sat to pee. He didn’t have any tools that might get it off, but he was also scared he might hurt himself. He almost pushed a nail file through his dick as he tried to pop the lock. He spent a very uncomfortable night. At the shoe store, every time he knelt to help a customer, he thought they would see the cage pressed against his slacks.
It made for a very long day, particularly when Mrs. Jones and her two daughters came in. He had a slight crush on one of her daughters, twenty-year-old Jeanette. Both girls were lovely and took after their mother, she was an attractive older woman of about her mid-forties. Jonell was pretty, but Jeanette was striking. They came in about every couple of months and he always loved kneeling before them, their legs were amazing and they featured in his mind every time he jerked-off at night. He thought Jeanette knew how he felt because she always seemed to give him a peek at her panties as he fitted new shoes. Today it was an exercise in discipline because each time he knelt in front of Jonelle, his cock tried to stiffen uncomfortably. Mrs. Jones made things worse and she couldn't make up her mind and kept stroked her stocking-clad legs. He almost cried when Jeanette flashed him again. He wasn't sure why, but she pulled her skirt up higher than ever and he got a painfully long look at her raspberry-colored panties. It made it a very long and extremely uncomfortable day.
He dreaded going to a locksmith and trying to explain it. His imagination might have been lacking in sexual matters, but he had no problem as he imagined the look on some locksmith’s face when he dropped his pants and showed the lock he needed to be opened. The locksmith would probably laugh and kick him out. He thought maybe he should find a female locksmith, but with his luck lately, she would be a knockout, and every time she tried to touch him, he would be in agony. The worst-case would be she might like him caged as JJ obviously did and refuse to remove it. He imagined a locksmith who looked like Jeanette making him eat her pussy and — a spasm of pain went through his groin as his cut off that line of thinking quickly.
He knocked on the door, but there was no answer. He debated camping out by the door when her neighbor came out. Normally he would have just stopped dead to stare at her, but in his misery, he barely noticed the attractive purple-haired woman. She was tall and well-built with long legs peeking out from under a silk robe. Her skin a dusky color that would have reminded him of cinnamon, if he had been paying attention.
“Can I help you?”
He turned at the throaty voice and smiled a wan smile at her. “I’m looking for JJ?”
“I don’t think she’s home yet. Are you planning to wait for her?”
“I think so.”
"Why don't you come in here. We'll hear her when she gets in. The walls in this place are paper thin." She said smiling.
He accepted gratefully and followed her in. He was surprised how tall she was, easily topping him by several inches not counting her high heels. That's when he noticed her long legs. The colorful robe had swirled around as she turned and drew his attention to her body. He felt his groin getting a little uncomfortable as he prayed JJ would hurry home.
“I’m Tonya, by the way.”
"Jonathon, I'm pleased to meet you."
“Can I get your something to drink?”
“Water would be fine.”
She came back in with two glasses of wine. “If you are going to beard JJ in her den, you might need some reinforcement.”
He smiled at that as Tonya went on.
“She had a wild time last night, I can tell you that!” Then she saw him blush. “Oh my god, that was you? I didn’t mean to embarrass you, but I did say the walls were paper thin. Don’t feel bad, you two fueled my own fantasies all night. I was alone, but you made me feel like I was watching. She’s a wild one!”
He couldn’t say anything. He just reflected on some of what he remembered from last night. The cock cage grew even more uncomfortable. He desperately wanted it off!
Tonya studied him closely. “I hate to pry — no that’s not true, I love to pry. But after what I heard I have to know, are you still wearing it?”
He wanted to melt into the cushions as he felt his face heat up.
Tonya clapped her hands. “Oh, that is too precious! I know this is stretching things since we just met, but can I see it?” She loved the look of shock on his face.
He didn’t answer, he couldn’t answer.
“Look, I already know you have it on. It’s no big deal. I’m just really curious what it looks like. “
He didn’t say no, but he also didn’t say yes.
"I'll drop my top and show you my breasts if you show me your cock. Please, Jonathon." Without waiting for an answer, she shrugged out of the top of her silk robe, letting the tie catch it at her waist. Jonathon couldn't help looking. Her breasts were large and very firm with large aureoles. They were the type of breasts he remembered from the men's magazines he used to jerk off too when he was younger. They looked perfect. When her hands cupped them, it felt like the cock cage shrunk two sizes.
She sat there and worked over her breasts and Jonathon couldn’t look away.
“Please Jonathon, it’s such a turn-on for me, especially after hearing you two last night. I was so tempted to break through the wall.”
He relented, not totally sure why, but everything about her was impossible to resist. He undid his belt and pulled his pants down. She inhaled sharply at the sight and when he went to pull them back up, she stopped him.
“Now, Jonathon, here I sit topless and horny as hell. You can't cover it back up so quickly. You barely gave me a glance." She knelt in front of him, not letting him sit back down, and held his hips as she looked at his encased member. Her attention was doing a number on him, he felt the confines of the cage more than even last night. Then she pressed her face to his imprisoned dick and he felt himself jerk in response.
“Oh, I wish you were not locked up. I would love to suck your cock! I bet you would cum a bucketful!" She rubbed her face all over his caged cock as she held his butt cheeks and pulled him toward her. "You have no idea how fucking horny this makes me. I would suck your cock until you were ready to cum and then spray it on my tits. Would you like that?”
She looked up at him in time to see him nod.
"The real question is would you lick your cum off my tits? I have my kinky side too but don't worry, you won't find a strap-on in this apartment. JJ and I have a few similar fetishes, and I will admit she's pegged me too! She's really good at it. I have to know, did you enjoy it?”
Jonathon wasn’t sure how to answer that. He was getting really turned on, but he’s still not sure he really enjoyed what happened last night.
Tonya smiled. “Let me guess, you’ve never done that before?”
Again, he couldn't answer, but she saw the answer on his face.
"It's okay, I know it hurts a little, but believe me it gets better over time. I know a few guys who prefer it to pussy. Most woman's butts are tighter than their pussy, especially after childbirth. Take my word for it."
Tonya stood and pulled his face to her chest. There was an irresistible invitation and he feasted on those incredible tits. She slowly sat back down and he ended up on his knees sucking on her breasts. He really enjoyed it, even though he felt the cage shrink again. He knew he should stop, but how often do you get such chances?
“You are so good at that. Damn that JJ, I really want to fuck you!” Jonathon wasn’t sure he even heard her correctly. No girl ever said something like that to him.
She stood quickly, almost knocking him over. She held out a hand, “Come on, we’ll still be able to hear her from the bedroom.” He followed her quickly, once in there she stripped him completely and stood next to him, fondling his cage while kissing him. Then she led him to the bed and had him get on his hands and knees.
“I know she pegged you, but I know her. She used lube instead of eating your ass, but I bet she had you eat hers, didn’t she? You don’t have to answer, I can tell." With that, she licked across Jonathon's asshole and ate him like he had a pussy. In moments she felt him push back against her. That’s when she rubbed his caged cock again.
Jonathon felt some confusion, but he couldn’t ignore what he felt. If this is what JJ felt last night, he could understand some of what she had him do. Tonya’s tongue felt longer than it did when he was kissing her, but that was just because this was so new to him. She started tongue-fucking him while rubbing his taint. He couldn’t quite believe how good it felt and quickly came. He felt the orgasm more than he normally did. His body shook and his arms collapsed and he ended up face down on the bed. Tonya rolled him over and put her fingers to his mouth, the ones that caught some of his cum. He wasn’t yet able to think clearly as he tasted his cum again.
"See, baby, that wasn't so bad. Even in a cage, you can still enjoy yourself."
“I still want it off!”
"I do too, I can't wait to feel you in my ass!"
“You like that?”
“Oh, hell yea! A nice tight ass squeezing down! I'm pretty sure you would like it better now. You sure can’t tell me you didn’t like what we just did.” She said as she licked the remains of his orgasm from her hand. "I told you I am somewhat kinky myself! My all-time fav thing is to have a cock in my ass while I have someone else in front of me with their cock. I can suck while getting fucked at the same time. They don’t have to be two guys, JJ and a girlfriend of hers did that to me recently. It was fucking great!”
He was processing that when she said something that didn’t make any sense, “After all, pussy’s not for me.”
“Don’t you like getting fucked in the pussy?”
She smiled at him as she realized just how young and somewhat naïve he really was. To herself, ‘JJ really caught a newbie this time!’ Aloud she said, “Here let me show you.” She lifted and straddled his chest, then she untied the robe and let it fall behind her. He saw her beautiful chest again as the robe slid off her shoulder. Then her narrow waist and widening hips. Then he looked between her legs, he saw the largest clit he ever imagined. Then he realized it wasn’t a clit, but a very small, only about an inch and a half long soft cock.
He didn’t know what to do, part of him was scared, but it wasn’t like it was some big macho guy trying to fuck him. This was a lovely girl who wanted him out of the cock cage as much as he did. One who had great breasts and kissed so wonderfully.
"I'm glad you're not being stupid. "Yes, I'm a transwoman, the keyword being a woman. I live like this all the time, I love getting fucked in my ass, I love sucking cock and eating pussy and ass. I adore waking up in the morning and having early morning sex and sometimes I just love being thrown over the back of a couch and fucked until I scream!” She looked carefully at him, trying to gauge his reaction.
“In fact, if you were not caged, we might well be just like this.” She shifted back and straddled over his cock, pressing down on him. “Your cock would be in my ass-pussy and I would be riding up and down on it while playing with my own little cock.”
She did exactly what she said and lifted up and come back down on his cock while she used three fingers on her own. It almost felt like he was fucking her every time she came down on him. In a way, it was fascinating to him to watch her small cock harden until it was between two and three inches long and a bit wider. She suddenly shifted and was between his legs, pushing them higher. Her little cock pressed near his ass and didn't go any further. She spat on it and asked, “May I? It won’t hurt, I’m much smaller than JJ’s dildo.”
He was somewhat overwhelmed by all the sensations and when she touched the tip, he made an interesting noise. Tonya took that as a yes and pushed her cock into his ass. He felt it and she was right, it didn't hurt at all, in fact, it felt better than her tongue.
As she slipped inside, she laid down on him and kissed him as she stroked her cock slowly in and out. “God, you feel so fucking good! I knew you would!” She fucked him very slowly and watched him as all those feelings flooded through him.
She knew well that JJ was more concerned with her own pleasure and she wanted to make sure he enjoyed this. She hoped it might lead somewhere, after all, how often do you find a good-looking guy who enjoyed getting fucked in the ass and eat his own cum? If he sucks her cock, she was going to do her best to keep him! She hadn’t had a regular guy in a while and really thought he would be perfect. Besides, she could picture him being double-penetrated and that was almost enough to make her orgasm.
She lifted back up and told him to play with his cage, as she stroked herself and play with her breasts. She knew how sexy she looked and his facial expression as he looked at her told her that he thought so as well. She was hopeful, more so than anyone she had met recently.
She felt herself gett close and tried to slow it down, but she couldn’t. When she felt him tighten down on her, she came in his ass. Then she surprised him, by snagging something off her nightstand and popped in a small butt-plug to hold her cum in his ass. He barely reacted as he was about to cum again himself.
A few moments later, he did and Tonya was happy to reach over and lick and suck it all up. She then snuggled next to him, like to satisfied lovers. She felt him look over at the clock.
“Shit, she’s not home yet?”
“I guess not! She might have hooked up with someone else or simply forgot. She can be a bit flighty!”
“I need to go, I have to work tomorrow?”
“I have an idea,” Tonya said seriously. “Let’s go to your place and grab a change of clothes. You can spend the night here and hopefully catch JJ in the morning before you head for work. Besides, you don’t want to 'wham-bam-thank-you-ma’am' me do you?”
He flushed at that. “No, I wouldn’t ...”
Tonya laughed, “I’m just teasing ya. So what do you think of my idea?”
"I guess if you don't mind?"
She looked at him, “I generally don’t fuck everyone who comes by — what do you think?”
“I’m sorry, I’m just kinda confused at all this.”
She snuggled down next to him. “No worries, we can just let things happen as they happen. As cute as you are in a cage, I really want that cock free. You have no idea how horny I am to get well fucked!”
His arm went around her, “I guess it sounds like a plan. Certainly better than JJ’s bum’s rush. She barely gave me time to get dressed.”
“I can imagine, I’ve seen her do it before.”
“And you are friends?" He asked and sounded very curious.
"Oh, JJ's not perfect, but then neither am I. There are things she probably doesn't like about me, but we get along really well. To be honest, I'm not sure I approve of her putting you in a cage without the ability to remove it, but I do understand what a turn-on it is when you talk someone into doing things they might not normally consider. I mean look at us?”
There, she said it, ‘us’. She wasn’t sure how he would react to that and did everything but cross her fingers. Then he got up.
“Well, if we’re going to do this, I guess we need to hit my place.” She secretly thrilled at him using the word ‘we’.
So that’s what they did. They ran into one of his neighbors who took a long look at Tonya as she went past. Jonathon was kinda proud that he was with such a beautiful girl that others noticed. His last regular girlfriend was back in high school, since then it’s been minor hook-ups but nothing steady.
His place was a little messy, but not too bad. He grabbed a bag and a change of clothes for work, some toiletries and when he turned around, he found Tonya naked on his bed stroking her cock.
“I can’t wait for that lock to come off. Come closer, honey.” Jonathon looked at her, at her position leaning back against his headboard, her legs open wide. If a girl was in that position, he knew exactly what she wanted.
“Just stay there.” She said as she stroked. “You need to know what you are getting into with me. I am a girl in every sense of the word with this small little exception. I adore sex in all its forms and I do love the way you’ve opened yourself up to new experiences, both with JJ and me. But if you can’t handle this small part of me, I’d rather know now than invest a lot of time and end up losing you because of this! I have no plans for surgery, I take hormones, and these tits are as fake as an honest politician, but this pile-driving ass is all me!”
He stood there and looked at her and ran through everything that happened since meeting JJ. He didn't understand all of it, but if he was honest with himself, it wasn't all that bad, he was just surprised and overwhelmed. Although shocked might be a better word. If someone told him that twenty-four hours after meeting a sexy woman he would be standing in his own bedroom watching an even sexier transexual woman jerking her cock with a plug in his ass which kept her cum from leaking out, he would have laughed and called you insane.
As it was, he didn’t say anything. He simply knelt on his own bed and bent over to take his lover’s cock in his mouth!
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