Jonathon Learns Some Life Lessons
by Brookell
Copyright© 2021 by Brookell
Erotica Sex Story: Jonathon meets a woman who educates him, but then he meets her neighbor who excites him!
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa Coercion Consensual Romantic Heterosexual TransGender Fiction Anal Sex Sex Toys .
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 of 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 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 stroking 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 he 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 was 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 to 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?
To read the complete story you need to be logged in:
Log In or
Register for a Free account
(Why register?)
* Allows you 3 stories to read in 24 hours.