When Anthony arrived home shortly after midnight, he didn't know what was more frustrating – the way his date with Angela had gone or the fact that his parents were still "entertaining." The last thing he wanted after fighting with Angela was to have to make pleasantries with his parents and their well-heeled friends. Just three weeks shy of his eighteenth birthday, Anthony was still living at home, going through the motions of finishing his senior year. He and Angela had been going out for about six months and they were having "problems." Sexual problems.
Anthony strode in the front door and made a bee line for the stairs towards the kitchen. He had hoped to avoid having to make conversation but he heard his Mom call out to him.
"Anthony, honey. Come say hi to the McKensies."
Anthony breathed a heavy sigh and made his way to the living room. His parents and the McKensies were sitting on the couch and two easy chairs, drinking. The McKensies were old friends of Anthony's parents and he'd known them for as long as he could remember. Mr. McKensie was a lot older than his wife. He ran a consulting firm in the pharmaceutical space and spent a lot of his time travelling. His wife was a doctor, or psychologist, or something, Anthony wasn't sure. He had always found her attractive, in a slightly unapproachable way. She looked like the actress Joan Allen and wore her hair up on top of her head. She had a great body hidden under her rather conservative clothes.
His Mom spoke first.
"How was the movie? Did you have a good time?"
"It was fine. Hi Mr. McKensie. Hi Mrs. McKensie."
"Hi Anthony" the McKensies chorused.
"Are you hungry, dear? There's plenty of leftovers. There's some tri-tip if you want."
"That's okay. I'll just have some cereal. Nice to see you."
He gave a half smile and made his way into the kitchen.
"Anthony's been seeing Angela for six months now. She's a cheerleader..."
Anthony could hear his Moms voice trailing off. He pulled down a bowl from the cupboard and a box of cereal from on top of the frig. He was adding the milk when he heard someone come in the kitchen. It was Mrs. McKensie.
"Just getting some ice" she said as she made her way to the freezer. Anthony was replacing the milk so they did a little two step together trying to avoid one another. She let out a little laugh. Anthony just smiled.
"Tough night?" she said.
"You seem to have a little cloud over your head."
"Is it that obvious?"
"Well, it's kind of my job to notice things like that."
A sympathetic smile crossed her face. Anthony saw the kindness in her eyes and smiled back.
"Just girlfriend issues" he said, softly.
"Ah" she answered, knowingly. "Do you want to talk about it?"
Anthony leaned against the kitchen counter and shrugged.
"Sometimes it helps to get it off your chest."
"We're just not compatible."
"Incompatible in what way? Intellectually? Emotionally?" A long pause. "Physically?"
Anthony looked up.
"You don't feel that you're compatible physically? Is that it?"
Anthony stared at his cereal.
"You know, I don't think the answer is in your Cheerios" she said softly. He heaved a sigh and then looked up at her.
"We're not compatible physically and I don't know what to do about it. It's really frustrating and now it's coming between us."
"I can see that it's frustrating to you, Anthony. What seems to be the problem?"
"It's my problem. Not hers. It's all me."
"What about you, Anthony?" Silence again. She was obviously close to the root of the problem.
"Anthony. What is it about you that makes you incompatible physically?"
He swallowed hard.
Mrs. McKensie nodded slightly and then spoke in a practiced, reassuring tone. "You know, Anthony, there's a wide range of normal when it comes to size. Many men have concerns about it but the anxiety is unfounded. Because a woman's pleasure center is close to the surface, a small penis needed be an impedi..."
"It's not that."
"It's not that I'm too small."
"Oh. What is it then?"
"It's that I'm too big."
She looked at him for a moment, saying nothing.
Now she was the one glancing at her drink.
"You know, Anthony. If you'd like, I would be happy to talk to you, professionally, and help you deal with this...problem."
"You mean, like, counseling?"
"You could come down to my office someday next week and we could deal with this issue. I think I can help you."
Anthony didn't respond.
"You do want to resolve the problem, don't you?"
"Don't you feel comfortable talking to me?"
He looked up at her.
"Yes. Yes, I do."
"Then I think you should come down to my office next week. I can do this pro bono—at no cost. How about tomorrow after school? Can you come to my office tomorrow at 5pm? You know where my office is. I'm at the Cooper Building downtown."
"Yeah, I guess so."
"Good. Then I'll see you tomorrow."
And with that, she picked up her glass and went back to the living room. Anthony just stood there thinking "did that just happen?" Two days later, Anthony had trouble concentrating on U.S. History. In exactly 50 minutes class would be dismissed and he would be making his way to wrestling practice. Afterwards, he'd have to take the usual ribbing from the guys on the team in the shower. They called him "The Horse" or "the Italian Stallion." He had gotten that kind of grief his whole adult life and was used to it. What he wasn't used to was all the conflict with Angela. He had been patient for months for her to be "ready" to have sex and then when she was ready, they couldn't do it. It didn't feel right. It hurt too much. He wasn't doing it right. Sex was supposed to be fun and instead it was just a big drag. He liked her but he'd made up his mind pretty much to end it.
As he rode the bus downtown he thought about Mrs. McKensie. She was Mr. McKensie's second wife, a trophy wife. He got to know her when they joined his family on a ski trip. She must be in her mid thirties. She was athletic. She had raven hair and green eyes. She also looked great in a bikini. He knew that because he would watch her and her husband in the hot tub from the window in his room. She had full, round breasts and a firm body. The rich guys always get the hot wives.
When he arrived at her office, he entered what was obviously some kind of waiting room. There was a door open that seemed to lead to an office. He noticed there was no receptionist around.
"Anthony, you're here. Come in."
Anthony walked into the dark, well-appointed office. A walnut desk sat in front of a tall, curtained window; a couch lined the opposite wall. Persian rugs, throw pillows, and a bookcase with recessed lighting completed the look.
"Have a seat" she said, gesturing to an antique chair which faced her desk. He sat down, taking in the room. She took her seat behind the desk.
"How are you Anthony?" she said with concern in her voice.
"OK, I guess."
"I'm glad you came this afternoon. I've known you a long time and I'd really like to be able to help you."
Anthony sensed she meant what she said.
"Thank you. I appreciate it. You taking the time and everything."
"Why don't you start at the beginning. Do you mind if I ask you some questions? Do get context?"
"How long have you and your girlfriend gone out?" "About six months." "And how long have you been having issues with your sex life."
"Well, since we started having a sex life. I mean, since she decided that she was ready to, you know, do it."
"To have intercourse."
"And when did that happen? When she decided she was ready to have intercourse."
"About three weeks ago."
"And have the two of your engaged in intercourse?"
"Not really. We tried...but it didn't...work."
"What you mean 'it didn't work?"
"It was too painful."
"For her? It was too painful for her?"
She stood up and moved to the front of the desk, sitting on the edge.
"Anthony, do you know what foreplay is?"
He shifted a bit in his seat. "Sure I do."
"Do you engage in foreplay before you try to have intercourse?"
"Can you tell me what it is you do? For foreplay?"
Anthony's face grew redder.
"We kiss. For a long time. To relax her. Then I touch her. Gently. On the breasts. And on her...vagina. And then I lick her."
"You engage in cunnilingus?"
"And does your girlfriend enjoy it when you do this?"
"Yes. She says she does."
"How long would you say you perform cunnilingus? On average."
"I don't know."
"Thirty minutes. Maybe longer."
She furrowed her brow slightly.
"And what happen when you try to penetrate her?"
"She says it hurts too much. I try to go slowly but she says it hurts and she wants to stop."
She nodded her head.
"It seems the problem isn't inadequate foreplay."
She was pacing now, thinking.
"No, the problem lays in the disparity in the relative size of the genitalia."
"Either you're too big or she is too small."
She turned to face him.
"Anthony. I'd like to do an examination. It's the only way to be sure."
"I need to collect some data before I can determine the recommendation action."
Her tone became very businesslike.
"Anthony. Take off your clothes."
"I need to examine you. Please take off your clothes."
"Anthony. You do want me to help you, don't you? Now, do what I say."
Anthony began to unbutton his shirt.
"I just don't see..." he stammered.
"Anthony, it's important that I'm able to get all the information in order to help you. Do you understand?"
Anthony was pulling off his shirt now. He had a chiseled chest, with well-formed pecs and strong, muscular arms. The benefits of wrestling. He began to pull down his jeans. His legs were equally strong, with thick thighs and well-developed calves. He was wearing boxers, which he left on.
"Now Anthony, I need you to completely disrobe. You can relax. I'm a professional."
She turned a light so that it shone on him. Bashfully, he turned his back to her and pulled down his boxers and bent over to pick them up. He saw his perfect butt strain and flex with the movement.
"Now turn and face me."
Slowly, turned. As his penis came into view, she felt her heart leap. It was long and thick. Longer, in fact, than any she had ever seen. It seem to hang half way to his knees.
"Anthony, are you aroused?" she asked directly. Anthony glanced down at his crotch.
"You mean. I mean. Um. Is this your normal...is this your penis in its flaccid condition?"
She was silent now. She walked slowly around him.
"You do have a penis that is on the larger end of the spectrum. Now, when you become engorged does it increase significantly in size?"
"Does it get bigger when it's erect. I mean, much bigger? How much bigger does it get...when it's erect?"
She was stammering now. Being in close proximity to this gorgeous young man was obviously getting to her.
"I don't know exactly. Bigger."
She came back around to stand in front of him.
"Anthony, I need to see your penis in its erect state."
"I really need...it's important for me, to do my job, to be able to see how big you get when you're aroused. Do you understand?"
"Now why don't you lay down on the couch here. Come. Lay down on your back over here."
She assumed a seat in a chair just out of his view, yet she had a complete view of his naked body.
"Now Anthony. I need you to make yourself hard. To masturbate."
Anthony gulped and hesitated.
"Anthony, you do masturbate, don't you."
"Fine. Now I need you to masturbate so that your penis will become erect. Go ahead. I'm waiting."
Anthony reached down with his right hand and held his penis and started to stroke it. She watched the member growing in his hand. It was already much bigger than her husband's penis when it was fully erect. Instinctively, her own hand went to her face, her finger to her mouth.
"Just imagine you're laying in your bed. You're all alone and you're touching yourself. Let your mind go. That's it."
His hand stroked his growing cock and she could see the head swelling and the veins becoming more prominent. She could feel her heart pounding and her hand started to drift down to her breasts. She was rubbing her nipples now, just as he was rubbing his cock. After a few minutes of this, his cock had grown significantly in both length and thickness and her pussy was hot and wet.
"Are you fully erect now?" she asked, her voice more breathy than usual.
"Um, no, not really."
"You mean, you get bigger...I mean you have more to go?"
"Well, I'm not used to this. It's kind of difficult."
"Of course, I realize this is unusual. What do you normally think of when you masturbate. Do you look at magazines? The internet?"
"Magazines, I guess."
"Well, I don't keep those kinds of magazines here, Anthony. What kind of pictures do you like to look at when you masturbate?"
"You know. Um. Women. Naked women."
"What kind of women do you like to look at. Perhaps if you visualized that it will help you become completely aroused. What do you like to look at?"
"Good. Think about a women's breasts then."
Her fingers were under her bra now, rolling the hardened nipple, as she spoke. She could hardly keep her mind on the dialogue.
"Do you like full breasts, Anthony? Full breasts with big, upturned nipples?"
He was stroking a bit faster now and she could see he was growing longer.
"Would it help if you could see full breasts with big, hard, upturned nipples?"
She moved next to him, kneeling on the floor.
"Would it help if you saw my breasts, Anthony?"
"Yes, I think so."
She started to unbutton her blouse. She pulled it off and revealed a lacy black bra beneath. She reached back and unbuttoned the bra and shook it loose. Her breasts were full melons and the nipples were indeed big, hard and upturned.
"I need you to be fully aroused for my examination, Anthony. I need to see your cock...er, your penis, at its very biggest. Would it help if I played with my nipples? Like this?"
She took each hand and slowly started to massage the nipples, letting them slide between her fingers.
Anthony was starting to breath heavily. His cock was standing straight up now.
"What else would help you? What else would get you completely aroused?"
"Well, my hands getting a little tired. Maybe if you....if you took over.?"
"That's a very good idea, Anthony. I think such stimulation could be very effective. If you're comfortable with that then I am too."
She sat up on the edge of the couch looked down at his cock. It was enormous already. She reached down and took it in both her hands and began long, soft strokes that pulled the skin both up and down. He had a circumcised penis and she spent time running her hand over the head. It reminded her of a big purple plum, firm and juicy. She wanted more than anything to take that fruit into her warm, wet mouth.
"How does this feel, Anthony? Are you close to your full size?"
"I'm going to stimulate you with my mouth now. You don't mind, Anthony? If I use my tongue and my mouth to stimulate you?"
She began to lick him around the tip, along and under the ridges, and down the length of his shaft. His body began to writhe beneath her. After a while, her lips surrounded the tip, her tongue playing with the tiny hole, while her hands continued their inexorable stroking. She opened her mouth and let the huge tip enter her. Her eyes closed and she slowly slid the tip in and out her mouth. He moaned audibly.
"Now, I'm going to try and take you into my throat. To swallow you."
And with that, she relax her throat and took his hardened cock deep into her throat. It was then that she finally appreciated just how large his cock was. She couldn't take it all the way, just partly, and even then her mouth needed to spread widely to accommodate him. She did her best to slide him in and out of her throat, her tongue flicking his tip on the way up. Finally, she lifted herself off and his cock stood straight up, glistening. It was huge.
"There. I think now you are fully erect."
"Yeah, I think I am."
She held his cock in her hands. She took her tongue and licked the entire length.
"Anthony, there's no question that you have a very large cock. It's not only longer than most, but it has a wide diameter, it's thick. But there is no reason whatsoever why you should'nt able to have a healthy and happy sex life."
"Absolutely. You just need to find the right woman. And you need to learn to use it with care. It's a gift, Anthony, and some woman is going to feel like she's the luckiest woman in the world."
"That's nice of you to say, but I'm not sure I believe it."
"Anthony, it's true. You saw the way I took your fully erect penis into my mouth and swallowed it. In the same way, a woman's vagina can take you all the way inside her. You will spread her, to be sure. Especially when your tip, when it's swollen like this, pushes into her labial lips. She'll feel like she's being forcibly penetrated. And when the base, the thick base here, when it enters her and her vagina is filled like it's never been filled before...You may find that woman will cry out, in a mixture of pleasure and pain. And if you thrust your cock into her again and again, deeper and deeper, faster and faster, you may find she'll actually scream. Scream as she cums, again and again, filled by your big, hard, glorious cock."
She had been slowly stroking him as she recited this, lost in a reverie.
"Would you like me to show you?"
"This is beyond the bounds I would normally do in a therapy session. But for educational purposes.."
"I'm willing if you are."
"Very well, then. But you must do exactly as I tell you. Understand."
She smiled. "First, you must call me Charlotte."
"OK. Charlotte." He smiled back at her.
"First I want you to undress me. You may kiss me while you do it."
He did as he was told, pulling off her skirt and revealing the sexy black panties underneath. Slowly he pulled them off too. All the while they kissed hungrily, their tongues intermingling, their hands on each other's bodies.
"Now lay back" she commanded. "I want to sit on top of you while you eat me out."
Sure enough, she straddled him and rode his face while he performed cunnilingus. She was already so turned on that her pussy was hot and wet as his tongue entered her, probing, licking, caressing, and flicking her clit. He did it for a good quarter hour and brought her close to orgasm.
"Now I want you to suck my breasts and finger fuck me."
She lay on her back and spread her legs, one up on the back of the couch. He took her extended nipples, one at a time, between his lips and sucked them. Meanwhile his fingers probed her pussy while she instructed him.
"Now use three fingers."
"Don't forget the clitoris."
Her pleasure grew until she tipped over into orgasm, writhing and wimpering on the couch. More importantly, she was readying her pussy to receive his cock.
"Now I don't know how you've been doing it, but there's no way I'd let you shove that monster in me straight away. We're gonna start with you on your back and me on top. That way, I can control how far and fast we go. Got it?"