John and Erin
“I’m going to come!” John said, desperately.
He heard a resigned sigh in his ear.
“Not again…” Erin complained, as he spurt his load into her pussy. As soon as he finished she pushed him off of her, irritated.
“All three times we’ve had sex now you’ve come within a minute, John. I really tried to give you the benefit of the doubt, even after I saw how small you were, but I’m not sure if this is going to work out.”
John winced. One of the things that first attracted him to Erin was her brutal honesty. When they met, through mutual friends, the first thing she said to him was that he was cute, but his shirt was the wrong color for him. He thought it was a very unusual thing to say to someone you just met, and it intrigued him enough for him to start pursuing her, even though he was reasonably certain she was out of his league. Erin was tall, about the same height as him, with jet black long straight hair and green eyes. Despite her slender figure, she had generous firm tits, and always showed them off to great advantage with low-cut tops and dresses. To his surprise, Erin had agreed to go out with him after just a few tries. On their first date, he could feel the eyes of every guy in the restaurant on her cleavage – she had worn a tight dress that was cut so low he could see the lace of her bra. He figured this was a small price to pay for being with someone so sexy, and felt a sense of pride that she was out with him, despite all the attention she was getting.
He wasn’t completely caught off guard by Erin’s comment – she had dropped hints over the last couple of weeks that he wasn’t satisfying her. He felt immense pressure to get her to orgasm, and that didn’t help with his old problem with premature ejaculation. He was completely infatuated with her though, and desperately thought of ways to avoid her dumping him.
“I’m so sorry Erin – I know I have a problem with that. I’d do anything, though, to make you happy!”
She turned over on her side, facing away from him.
“I know you’re trying your best, babe” she said. “Listen, I like you. If I didn’t I wouldn’t have gone out with you again after that first time.”
John winced again at the memory of their first clumsy sexual encounter. They were making out on his couch after their second date – he was lying on top of her, with his hand under her shirt, feeling the breasts he had been lusting after since he met her. He was rock hard, and he was sure she could feel him against her thigh. She shifted her position so they were more side by side on the narrow couch, and unbuttoned and unzipped his pants. Reaching her hand underneath his jockeys, she pulled free his dick. He had gasped with the contact and struggled to remain calm. He saw her look down at the penis in her hand and frown at what she saw. He know he was on the small side, and his cheeks burned with shame in her reaction. She started rubbing her hand against him, and to his continued embarrassment he came within just a few strokes.
“Ok…well, how do you feel about oral sex?” Erin asked, still facing away from him.
“Um, good, I guess?” John said carefully.
“Ok, well I don’t suck dick. I don’t buy into the male dominated paternalistic bullshit that I should suck you off and swallow your cum. BUT I do enjoy getting eaten out. So…”
With that, she turned over, and spread her legs suggestively.
“But…I just came in your pussy…” John protested. “I don’t know…”
Erin sighed. “Look. You can’t make me come with your small dick. This is pretty much your last chance. If you can get me off with your tongue, then maybe I’ll go out with you again. If you can’t, then this is pretty much it. I need to be with a guy that can get me off.”
Seeing the logic in what she was saying, John slid down to get between her legs. Her pussy was trimmed neatly, with just a small strip of pubic hair. He licked her tentatively, fighting down a shudder. He had never tasted his own cum before, and now he was about to get a mouthful of it.
Erin sighed and wound her hand in his hair, pulling him tighter against her. He felt his mouth and nose push into her womanhood. He inhaled the scent of her pussy mixed with the smell of his own spunk.
“Put your tongue inside me” she commanded, arching her back slightly and pulling him even closer into her. He extended his tongue and slid it into her. He tasted his own sperm mixed with her juices. She thrust her hips up and back, sliding his tongue in and out of her slit.
“Hmm…that’s a good boy. How does your jizz taste in my pussy?”
John muttered an intelligible reply as he continued to fuck her pussy with his extended tongue.
“Now lick my clit. Make me cum and I might go out with you again”
He slid his tongue up her pussy. Finding her clit, he flicked it with the tip of his tongue repeatedly.
Erin moaned and tightened her grip on his hair. Excited by the fact that he was finally getting her turned on, John licked and sucked her clit in earnest. Doing this, his own inadequacies melted away – he wasn’t under pressure to last a long time during intercourse, and his below average penis size wasn’t a factor at all. He could lick her pussy until she came, and that was the most important thing now. He still tasted the funk of his cum in his mouth, but tried to ignore it as much as possible and concentrate on the job at hand.
Erin’s legs lifted and she crossed her ankles across his back. Her thighs squeezed against him almost painfully. He could no longer hear her moans and heavy breathing – his entire world narrowed to just his tongue and her pussy. He alternated between flicking her clit with his tongue, running his tongue up and down her slit, and sucking. He felt his tongue and jaw begin to ache with the prolonged effort.
Minutes later Erin went rigid and let out a little scream. Her hands tightened painfully in his hair, pulling his face against her. Her orgasm went on for a good 8 or 10 seconds before she finally relaxed and let him go.
Exhausted, John lay back, resting his head against Erin’s thigh. He could feel her juices covering his face, as well as a good portion of his own cum. She reached down and began lazily running her fingers through his hair.
“That wasn’t bad for a first time, John. It took you longer than it should have to get me off, but in the end I had quite a nice orgasm.”
Despite himself, John felt a flush of pride at her words. He had to admit to himself it felt great to get her off, even if it was by eating her out instead of fucking her.
“Thank you, Erin. Does that mean you’ll go out with me again?”
Erin was quiet for a minute.
“I don’t know, John. I don’t want to mislead you – I have no interest in letting you fuck me again with that pindick of yours.”
John winced again.
“Oh, well…um, I could go down on you instead, I guess? I mean, I do whatever you want me to do” he said desperately, looking up at her.
“Hm..I like that” Erin said, pulling him up to her and kissing him, her tongue finding its way inside his mouth. “Yes, I’ll let you take me out again. And I’m going to hold you to that last part.”
Three days later, she sent him a text. “Pick me up tomorrow. 6 PM. Sharp.”
John spent some time cleaning his place. He didn’t know what their plans were – she didn’t send any more details. If they ended up back at his house again he wanted everything to be perfect. After showering, he put on a pair of jeans and a nice shirt and sportcoat. He didn’t know if they were going someplace casual or dressy, but figured he’d have either contingency covered. He was outside of her house at five before six, but waited in his car until exactly 6.
Erin answered the door. She looked stunning – a tight white minidress showed off her ample cleavage, and was cut so short that he was amazed he couldn’t see her panties.
“You like?” she asked, smiling at his obviously lustful gaze.
“Um, yes..” he stammered, finally tearing his eyes from her exposed breasts.
“Glad to hear it.” she pointed at a small shopping bag near the wall.
“Give me a hand with that, would you? I’ll lock up.”
He held the car door for her, then hurried around to his side. Starting up the car, he asked where they were headed.
She turned and gave him a sly smile.
They made idle chit chat on their way back to John’s house. She mentioned that some friends of hers were meeting up at a bar later that evening, and that maybe they’ll be joining them. Arriving home, John quickly unlocked the door. Erin immediately walked to his bedroom, with John eagerly following. Once there, she put the bag on the floor and turned to him. Her demeanor had changed – she was no longer the girlfriend on a date – she was a tall, beautiful woman completely in charge of the situation.
“Take off your clothes” she said, quietly but authoritatively.
“What? Um..are you going to also..?” John said, uncertainly.
“You said last time that you would do whatever I wanted. What I want you to do now, John, is take off your clothes.” She crossed her arms across her chest and arched an eyebrow at him.
John decided he had better obey. He hurriedly pulled off his sportcoat and shirt, then pulled down his pants and socks. In a few seconds he was standing in front of her in his boxers.
She merely looked at him with her arched eyebrow. Getting the hint, John slowly lowered his underwear to his ankles, then kicked them off. Awkwardly, he held his hands in front of his penis. He felt himself growing hard.
“Hands at your side, John.”
Slowly, he complied, losing the last shred of covering he had. He was completely naked, his erect cock sticking out in front of him. He took a huge amount of willpower to not try to cover himself.
Erin started to slowly circle around him, inspecting his body from all angles. John couldn’t help but feel like he was some sort of prized animal being inspected by it’s owner. She stroked his ass, felt his arms, and ran her fingers slowly down his back. He heard her voice from directly behind him.
“You don’t have a bad body, John. Nice and thin, nicely formed muscles, cute butt.” With that, she smacked his ass cheeks hard, forcing him to draw in a breath sharply. She completed her circle, standing in front of him.
“Except, of course, for this” she said, looking down at his still erect penis. He looked down too, mostly in humiliation. His dick was standing at full attention, as hard as he had ever been before. He admitted that she was right about it’s size. He was definitely below average in length and thickness. He had never heard it directly from previous girlfriends, but knew from their reactions when they first saw it and from his own research on the internet. He thought about all the times he had seen hung guys with thick substantial cocks in porn, and wondered what it must feel like to fuck a woman until while she comes again and again on your huge dick. He knew that he’d probably be fucking Erin right now, instead of standing on display, naked in front of her.
She reached down and poked it with her finger.
“I don’t really want to touch it, much less have it in my pussy” she said. Suddenly, she flicked the head of his penis hard with her index finger. He inhaled sharply at the sudden pain, instinctively bending forward to try to protect his sensitive parts. She held her thumb and index finger right in front of his dick, ready to flick him again.
“Do you think your tiny pencil dick deserves to be in my pussy?” She asked, threatening his cockhead with her finger.
“…no” he admitted, hanging his head in shame.
He winced in pain as she flicked his cock again.
“No what?” she said sternly.
“No..ma’am?” he said, uncertainly.
“Good boy. No, your pencil dick does NOT deserve to be in my pussy. How many times have you been able to make a woman orgasm with your pathetic penis?” Her hand was back in position again, ready to inflict another painful flick on his cockhead.
He could feel a red blush of shame creep over his face.
“Um..none. Ma’am” admitted.
“I didn’t think so. Now do you think YOU deserve to cum?”
“I don’t think so either. Do you think it’s MY job to please you sexually?”
“Oh no, of course not, ma’am” he said hurriedly.
“Good. Do you think your mini dick deserves any type of pleasure at all?”
John hung his head again, feeling defeated.
His face reddened even further with the humiliation.
“My mini dick doesn’t deserve any type of pleasure at all, ma’am.”
She nodded again.
“Good boy. I’m glad we got that straightened out. I think that was an important step for you to take if we are going to be able to continue to date.”
She walked over to the bag she had brought and pulled out a small box.
“I’ll be right back. Don’t move.”
With that, she left the room. John stood naked in the center of his bedroom, fighting the urge again to cover himself with his hands. He could hear her in his kitchen, rummaging in the refrigerator or freezer. In a few seconds she returned. She was tossing what looked like a bag of frozen veggies in her hand. She was carrying the small box in the other.
“Lie back on the bed now, John.”
He complied, stretching out on his back.
“I see your little guy is still excited. We need to change for what comes next.”
She sat down next to him, and calmly placed the bag of frozen vegetables directly on his dick and balls. John gasped from the shock of the cold on his most sensitive part, and fought the urge to wriggle his hips to slide the icy bag off.
“Now we just let that sit there for a minute or two, and you’ll be all nice and soft.”
“Be a good boy and unzip me, will you?” she said, as she turned her back to him and pulled her hair to the side.
John eagerly unzipped her dress. The thought of seeing her perfect body naked distracted him from the growing discomfort in his dick and balls. Erin stood up and shimmied out of her tight white dress. She was stark naked underneath. John groaned when he saw her beautiful pussy so close to him. She sat down next to him, her thigh pressing against his side. She held up the box.
“So we decided that because of your inability to please me with your dick, you don’t deserve any pleasure from it either, didn’t we?”
“Yes ma’am” he responded, feeling the now familiar flush of shame again.
“I discovered a solution that will work for both of us. This will make sure that you don’t get any ideas about using your cock, and ensure that you focus on pleasing ME. You DO want to please me, don’t you?” She cupped her breast with her left hand and slowly started stroking her nipple with her thumb.
“Oh god…yes, I want to please you.” John gasped.
“Good boy. I got you a special chastity device” she giggled “special, because it’s the smallest size they make. It will stop you from getting an erection, I mean, if we could even tell.” another giggle, and she moaned slightly as she continued to rub her now erect nipple. “And you won’t be able to have an orgasm, which you selfishly had with me but weren’t interested in reciprocating. Now you’ll be more focused on me.”
She stopped rubbing herself and picked up the frozen bag.
“Aw…poor little penis. Looks like you’re all shriveled up from the cold. Now we can get your new equipment installed. Now, keep your hands at your side and DON’T MOVE.”
She turned around and straddled John. He could feel her ass and naked pussy against his chest. He felt her open the box, but all that he could see was her black hair cascading down her back. He loved the feeling of her pressing down on him, and imagined what it would feel like if she just moved down his body and slid his dick into the pussy that was now firmly pressed against him.
“Got to move quickly, before you try to get hard again” she explained. He felt her grab his dick and balls and shivered with the contact. He couldn’t tell exactly what she was doing, but he felt a few drops of some slippery substance being matter of factly rubbed around his flaccid member. Then his balls were pushed, a bit painfully, through some sort of ring, and finally she slipped his penis into some sort of cage. He heard a snap as she connect things together, and a metallic click. Finished, she looked over her shoulder at him and smirked.
“You’re in your little cage now, John. You should get used to how it feels. If you want to continue seeing me, this thing is staying on. After you’ve shown me you can focus on my needs, I’ll think about unlocking you once in awhile. Until then, the key stays right here.” She held up a simple gold necklace with a key attached. She slipped it over her head, and he knew that the key to his chastity cage was currently nestled between her gorgeous tits. He let out a small moan at the thought, and he felt his warming dick start to expand. The unyielding cage of the device was tight, and he felt that he could only expand the tiniest amount before his erection was cruelly denied.
“Last time you took quite a while to get me off, John. That’s going to have to change.”
She leaned forward until her face was just inches from his trapped penis. He could feel her breath on his balls, but not on his contained member. She slid back until her pussy was just inches from his face. He couldn’t help but stare, entranced. Her ass and pussy were just out of reach of his tongue.
“I’m going to have to train you.”
With that, she lowered herself down to his kinetic tongue with her legs bent, her heels by his ears, in a 69 position. He slipped his tongue into her slit, penetrating a couple inches into her. He felt her sigh, and she wriggled slightly, getting comfortable on his face. He slowly fucked her with his tongue, sliding in and out of her pussy and feeling it getting wet. Again, her hips and thighs sealed out everything from his world except his tongue and her lips, slit and clit. She started slowly grinding herself on his face, and he started to give her long, slow licks from her hole to her clit.
Suddenly he grunted in pain, as he felt a hard smack against his balls. He realized his arms were trapped by his side by Erin’s long legs. He wondered if he could throw her off of him if he tried, but then quickly realized he didn’t want to. He felt completely used, objectified and shamed. Yet gone was the terrible stress that came from trying to please a woman with his dick. He was stripped down, mocked and his penis was locked in a device, but he felt somehow at peace. All he had to do was follow her directions, and she would be satisfied. He was completely infatuated with Erin, and realized his words from their last date were completely true. He would do anything she wanted as long as she stayed with him.
He felt Erin breathe faster and she began to grind herself more against his face. His tongue, still sore from the other night, was starting to ache again, but he focused his attention on her clit. Giving it small licks, as much as he could with her pressed against him.
Suddenly he felt another painful smack on his balls, followed rapidly by a second. He moaned sharply and would have doubled over, if Erin’s naked body wasn’t trapping him. He heard one word barked sharply above him, muffled by her thighs.
He renewed his assault on her clit with his tongue, exhausting his poor tongue. He felt the juices from her pussy coating his face. He smelled and tasted nothing but her.
Three painful slaps on his balls, one right after the other, made him cry out in pain and surprise. He understood what she was doing now – the longer it took him to get her off, the more pain his balls would suffer. He redoubled his efforts, ignoring the pain in his tongue as he frantically licked her pussy. She was moaning now, and her legs were clamped tight around his head. He could feel her breasts sliding back and forth on his belly as she rode his face. She was slick with sweat and she slid on his body easily.
“You’re…taking…too long” he heard her gasp, and felt her grasp and hold his aching balls in one hand. She started giving measured, strong slaps to his already throbbing nuts, spaced just a few seconds apart. Desperate to avoid this punishment he furiously rubbed his tongue against her pussy. The pain seemed inescapable. He felt her start to shake above him, and she was gasping loudly. She suddenly stiffened and ground herself one last time onto his mouth. She screamed loudly. At the same time, her hand tightened into a vice-like grip and he gave a muffled scream. Her grip loosened only as her own orgasm finished and they both relaxed, exhausted.
Erin lay on top of him for minutes, her hand still wrapped around his injured scrotum. John knew he’d be aching for days from this treatment. Yet at the same time he felt a sense of peace and contentment. He had followed her directions and gotten her off, and he felt she was pleased with him. His face was still surrounded by her pussy and he felt like he was in heaven.
Eventually, she stirred.
“You’ll learn to do that better, John, but that wasn’t too terrible. I had a wonderful orgasm. Now lick me clean.” She rose up slightly, until she was an inch or so off of his face. He gave her pubic area long, slow licks, tasting her wetness and cleaning all of the fluid off of her. After a minute, she stood up. He saw her gorgeous body, and again his penis tried to expand in vain. He saw the key dangling from the cage, directly between her breasts.
“Now for your last present!” she laughed, reaching into the bag again. She pulled out a pair of pink panties. “Put these on.”
“What?” John asked, rising up to one elbow. “But those are panties…”
“Yep” Erin laughed. “Men’s underwear has space for a nice healthy package in front. Panties are small and smooth. Perfect for you, don’t you think?” She tossed them down to him.
John stumbled to his feet. Looking down, he saw a smooth steel tube where his penis should be, locked to a tight ring behind his balls. He didn’t see a way that it could come off, without the key around Erin’s neck. Feeling his ears burning in shame, he stepped into the panties and slid them up. They felt very different – slick and smooth. They were bikini cut, with just a thin piece of material around his hips. The pink satin fabric had a tiny ribbon bow in the front. To John’s continued embarrassment, they seemed to fit well.
Erin laughed and hugged him. Her naked body pressed against his, except for the steel barrier around his penis. She stroked his ass through the panties.
“They look so sexy on you” she giggled. He looked down.
“Before our next date, you are going to throw out every single pair of underwear you own and replace them with panties. You’ll buy these by yourself, in person, and I had better like them, understand? You will model them all for me. Think frilly, feminine, sexy – the kind you liked to see on the poor frustrated women you used to date.” she giggled again.
“Now zip me back up” she said as she handed him her dress. “We need to get ready to go out.”
They got dressed and ready. John kept stealing glances at his beautiful girlfriend, overwhelmed with his complex feelings. His jaw, tongue and especially balls were aching painfully, but he was ecstatic to be with Erin. She had brought a small overnight bag, and told him she would be staying the night at his place. He was looking forward to spending the night with her after their night at the bar.
He drove them to the bar to meet up with some of her friends. She was in her tight dress, and he had put on a sweater and jeans. His panties felt strange under the jeans, and the tight tube around his dick was a constant reminder that he belonged to Erin. She kept her left hand in his crotch the entire drive, rubbing and tapping the steel device she had locked around him.
At the bar, Erin met up with her friends, and John felt a bit awkward. He wasn’t the most outgoing guy and found it difficult to keep up with the conversation. Erin had told him he wouldn’t be drinking either so he could drive her home, so he resorted to hovering in the background, enjoying being in the company of his beautiful girlfriend.
As the night went on, people drifted away until it was just the two of them plus one guy, Chris, that was there with the group of friends. John picked up that he and Erin didn’t know each other, but that he had dated a co-worker of hers a couple of years ago. Still feeling awkward, John mostly let Erin and Chris chat. Eventually Chris slipped off to visit the restroom.
“Aw, poor John – I feel like I’ve been ignoring you all night.” Erin slipped her arms around his neck, pulling him in for a kiss. He could smell the alcohol on her breath – he had bought her 3 or 4 drinks during the night and he could tell she was a bit tipsy.
“Thanks for being such a sweet guy and buying me drinks all night. Isn’t Chris hot?”
This sudden non sequitur caught him off guard.
“Um, I guess?” He hadn’t really thought much about it, but he realized Chris was attractive – tall, lean but obviously muscular through his tight sweater. He had a square jaw, blue eyes and neatly styled black hair.
“I’m feeling a bit naughty…” Erin whispered into his ear as she stroked his face with her fingertips.
“Chris slept with someone I know – Cathy at work – and she said he was sort of an asshole but he has a HUGE dick!” Erin giggled. “Aren’t women the absolute worst? I barely know her, but two margaritas at an office party and suddenly she’s telling me about her love life, in detail.”
Just then Chris returned, and again he and Erin started chatting away.
“Baby – could you get Chris and I one more drink?” Erin asked, patting John on the arm.
“Oh, of course – beer for you, Chris?” John asked.
“Yep – hey thanks man” Chris responded.
He walked down the length of the bar. Even at this late hour, with the bar relatively empty, he had to wait a few minutes before he could catch the attention of a bartender. He ordered the drinks, a beer for Chris and a glass of wine for Erin. When he walked back to the couple, her hand was casually placed on Chris’s chest. They were laughing and seemed to be enjoying each other’s company immensely.
John knew that Erin was flirty, and figured her loosened inhibitions from the drinks had brought out this quality even more. He felt like the definition of a third wheel, awkwardly holding their drinks while they joked around and touched each other on the arm, as if it was the most natural thing in the world.
“Hey John – is it true?” Chris asked, as he casually took the drinks from him, handing the glass of wine to Erin.
“Um…what?” John said, trying to play cool and fit in.
“That you’re wearing something…two somethings…rather…naughty?” Chris laughed, and Erin gave him a smug grin.
John felt his face turn beet red.
Chris laughed and put his arm around Erin. “Come on now, why don’t you show me what you’ve got there.”
John looked around, embarrassed. They were the only people left in that part of the bar – most of the crowd had cleared out. He looked pleadingly at Erin. His beautiful girlfriend has holding on to Chris’s waist and grinning at him.
“Go ahead, babe. Show Chris here what you’re packing.” She giggled slightly, obviously tipsy. “You not going to embarrass me in front of my new friend, are you? Come on, show us that you can be fun and have a good laugh with us!”
John was pretty sure they wouldn’t be laughing “with” him. Glancing over his shoulder to make sure no one was around, he quickly unbuttoned and unzipped his pants and pulled them down slightly, showing the pink fabric and the tiny cute ribbon on the front.
Chris and Erin immediately burst out laughing, and he felt his face grow even redder. Shamefully, he started to pull up his pants. Erin quickly put a hand on his shoulder to stop him. She leaned in close to him and whispered sexily into his ear. He could feel her breath and smell her intoxicating scent.
“That’s not all, is it, John?” She kissed his cheek, her lips lingering on him. Her arm was still around Chris’s waist, pulling him closer. “Why don’t you pull those panties down a bit and show him what a man who wears panties looks like. I’d be SO appreciative…”
John’s couldn’t tell if his ears were burning in shame, or with lust for this incredible sexy woman. He had no idea things were going to go this far when she locked up his cock earlier today, but he found it hard to resist her. Slowly, he slid the front of his panties down, until they revealed the metal tube encasing his penis.
Erin looked down at his small tube of steel, smiling approvingly. Chris leaned forward to get a better look, shaking with laughter.
“No shit…I thought she was full of it when she told me! Why would anyone…and it’s tiny, just like she said! Do you really fit in there? Damn…”
Erin pulled on her necklace, freeing the key from it’s spot nestled in her cleavage.
“And it only comes off with this” she said, laughing. “And I intend to hold on to it for a long, long time.”
Chris shook his head as John quickly busied himself with covering himself and zipping up. He didn’t know how to react – he was a confusing mix of embarrassed, horny and proud that he made Erin happy. He had never felt that way before – such a strong desire to follow a woman’s wishes and make her proud of him.
When he looked up, he noticed that Chris’s hand was firmly placed on Erin’s ass, cupping it through her tight white dress. She was smiling and winked at John.
“You know, I think Chris had a few too many drinks. You should probably drive him home as well. The two of us can just pile into the back seat and keep each other company.”
Chris smiled openly at John and winked at him as well.
“I think that sounds like a fantastic idea.”
To be continued…