The Freshman 2: Meeting WantToBeShaved42

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The Freshman 2


The Arrival

*knock, knock*
Barry stood at the door nervously, waiting. This was the moment he had been waiting for all week. He was stood at the door of WantToBeShaved42’s house, waiting for her the answer the door. The door opened and there she was, dressed in the same outfit that she had used for her profile picture.

”Come on in, cutie” she said.

Barry walked into the house nervously, knowing what fate awaited him. Inside her house was huge, it had beautiful art pieces on the wall and statues that must’ve cost a pretty penny. Barry had imagined what WantToBeShaved42 was like a lot over the last week but it didn’t cross his mind once that she might be wealthy. Maybe she was one those people he had heard about that had a ton of money and liked younger men.

They walked into the kitchen “sit down” she said. Barry sat down on a barstool at the kitchen island.

“You want a drink sweetheart” she said.

“I’m not 21 yet” Barry replied.

”Who am I gonna call, the cops?” she joked.

She headed over to the bar and poured two whiskeys, the traded small talk. Walking over to the island she handed Barry his glass.

“Drink” she said in an assertive tone.

“I can tell that you’re nervous, the drink will help” she continued.

Barry was nervous, not only was he going to lose his long locks but he was also going to lose his virginity to a sexy woman much older and experienced than him.

”So what’s your real name” Barry asked.

“It’s Penny, my name is Penny” she replied.

“And yours?” she said whilst running her fingers through his hair.

“It’s Barry” he replied.

“Well Barry, I’ll get you another drink and then we’ll do something about that hair” Penny said in a calm, seductive tone.

Flick of a switch?

Penny grabbed a chair from the dining table, this was where Barry was to sit whilst being shaved.

“Come” said Penny in a stern tone.

Barry downed the rest of his whisky and stood up and started to walk towards the chair.

”Lose the clothes” Penny said authoritatively.

The drink hadn’t kicked in yet, Barry didn’t even have a slight buzz. All he could feel was the burn on his chest from the whisky and the feeling of nerves in his gut.

“Did I stutter my words?” Penny said sarcastically.

Barry is still stood there frozen. Penny walks over to him and begins to undress him. Stood there completely naked Barry grabs the zipper on the front of Penny’s catsuit.

Penny slaps his hand away “How dare you” she said.

“I don’t want you touching me until that head is completely shaven smooth” she continued.

Penny grabbed Barry by the arm and forced him to sit in the chair. As Barry was sat down she stood behind him and grabbed him by the hair “I can’t believe you had the audacity to think you can touch me with this mop on your head. I don’t think so. I only let men touch me, and men don’t have hair like this”

Penny looked down at Barry’s lap and could see that he was enjoying himself judging by his erection.


Penny grabbed the clippers. “Are you ready?” she asked.

“Urm not really” Barry replied nervously.

“I don’t care, you’re well past due for this haircut. You don’t get to have a say” she said.

The clippers clicked on. Penny pushed down Barry’s head. She held Barry by his hair, with her fist clinched with his hair, lifting it off the shoulders. Penny had complete control over Barry, he couldn’t so much as move his head.

Penny started shaving at the back of head, starting behind Barry’s right ear. His long hair began to fall as it was shaved away.

“Ahh your cute neck” said Penny. Barry could feel a slight breeze touch the back of his neck. It’d be some time since Barry had hair short enough that you could see his nape.

”A man’s neck should always be showing, it should only ever be covered by his shirt collar. It’s the way a man should be, it’s sexy” Penny continued.

The tease

More and more hair fell from Barry’s head until his long hippie locks was buzzed into a short clipper cut.

“You look so much better already” said Penny, standing in front of Barry.

Penny was admiring her handiwork, looking at what had become of Barry’s hair. She ran her hands over Barry’s soft buzzed cut.

“We just need to get rid of this now” said Penny, alluding to the short clipped hair that remained on Barry’s head.

Penny grabbed a towel that she had left to steam and placed it over Barry’s head.

“You see, this will let allow me to shave you down straight to the scalp. There won’t be a hair left on this head” said Penny.

Penny wanted to reward Barry for allowing her to shave away his locks, but not fully until he was bald. She just wanted to give him a little teaser, but not too much given how aroused she was also by the sight of Barry’s hair on the floor.

“How about whilst that towel is opening up your pours I give you a little something?” said Penny.

“What did you have in mind?” asked Barry.

Penny bent down, grabbing Barry’s erect penis. “You see, this is mine. I can do whatever I like with it. I could suck it for you but where would be the fun in just giving it to you?”

Penny’s mouth moved towards Barry’s cock and her lips gently touched it. Kissing the shaft three times.

Standing up, Penny unzipped the catsuit ever so slightly. “You like these huh?” she asked seductively, referring to her breasts.

She grabbed Barry’s hand placing it on her breast. Barry didn’t know what to think. There he was with a towel on his head, about to be shaved completely bald, touching the breast of a sexy older woman for the first time.



Penny moved back behind Barry, with both hands rested on his shoulders. The steamed towel was removed from Barry’s head. Penny grabbed a barbering brush, swishing it around in a pot. The brush now covered in shaving cream was moved up and down Barry’s head, lathering him up ready to be shaved.

“All men should have this done” said Penny, pushing down Barry’s fully lathered head.

Penny with a straight razor in hand began shaving in a downward motion towards the nape of Barry’s neck. The rough sound of the razor shaving, as tight as to the scalp as Penny could get it was the only sound to be heard.

Barry had remained mostly quiet throughout his haircut, only speaking when spoken to. There was a neatly folded towel resting on his shoulder, with each motion of the razor Penny would wipe the shaving cream and hair from the razor onto the towel.

“This bald head is looking very sexy” said Penny, shaving away.

“There’s just something about being fucked by a man with a bald head” she continued.

Barry sat there quietly, enjoying the feeling of the razor on his head. It was quite the experience being shaved by a very sexy, dominant woman. Barry couldn’t help but start to masturbate.

Penny’s hand hit the back of Barry’s head as she seen him masturbate. “Did I say you could do that?” she asked.

“No, I just thought” said Barry.

Before he could finish his sentence Penny asserted herself “Well you thought wrong. Once this head is bald, I will take care of it. Until then you sit still whilst I shave you”

Being bossed around like that only served to arouse Barry further. He’d never seen a woman as assertive and sexy like this before.  Penny knew what she liked and she wasn’t afraid to assert herself to get it.


Penny likes him bald

Barry’s head now completely bald, Penny gave it a few soft kisses. Walking in front of him Penny’s hand moved across his shoulder and her heels hitting the hardwood floor.

Standing in front of Barry with a duster, she began wiping away the small hairs that had fallen on Barry.

“Look at that sexy bald head, you’re a real man now” said Penny.

Penny had been all business shaving Barry’s long hair to a clean bald head but on the inside she had been fighting back the urges that had been building.

She could finally have what she had been craving so desperately. The sight of Barry’s clean head only aroused her further.

Becoming a man

Penny grabbed Barry by the hand and led him towards the sofa, sitting him down. Stood in front of him, Penny unzipped herself fully, removing the leather catsuit that had clung ever so tightly to her womanly curves.

Penny bent down and began massaging Barry’s cock. It was the first time anyone but himself had touched it before. Barry leaned back into the sofa, closing his eyes and relaxing. He felt Penny’s warm mouth around his cock.

The only sound to be heard was the sound of the slurp as Barry’s cock left Penny’s mouth with each suck. Barry began to softly moan.

”I can see you’re enjoying this a little too much” said Penny as she stopped sucking Barry’s cock.

”I’ve made you look like a man, now let’s go make you a man before you ejaculate just from the blow job. I’m going to take your virginity now” she continued.

Penny got up off her knees, placing herself on Barry’s lap. Grabbing his cock, she placed it inside of her as she sat down. Barry’s hands moved towards her lower back and she began to bounce up and down on Barry’s cock.

Penny began to moan, her hand holding the back of Barry’s head. Her long beautiful hair hung over, falling on top of Barry’s bald head.

The morning

Barry awoke the next morning, next to a sleeping Penny. He felt like a man, the night before was incredible. Penny was such an amazing lover, as the experienced older woman she took the lead.

Barry thought it best to get ready and head on back to his college dorm. He didn’t wish to wake Penny, he thought as a one night stand it was best to be out of her way.

As Barry headed for the door “where do you think you’re going” said Penny, emerging from the bedroom in a beautiful silk robe.

”I have to get back” replied Barry.

“There will a lot of girls now on campus that will want you now that you look manly with your bald head. You’re not to so much as look there way, you’re mine now” asserted Penny.

“I want you back here every weekend to keep that head shaven. I’ve made you a man now, I have your virginity and I expect you to maintain that bald head for me” she continued.

”yes ma’am” replied Barry.

“Another thing before you leave, next week when you arrive at mine I’m taking you out. You’re a man now and I would like you dressed like one when you’re in my house so we need to get you fitted for a couple suits” said Penny.

Barry was taken back a little bit, he thought this was a one off thing but to Penny it obviously wasn’t that way. Not that Barry was going to argue, a relationship with a sexy, wealthy older woman that was built on sex sounded like a dream.

Penny handed Barry a watch, it must’ve been worth $2000. “This is to go with your suit that we’ll get you next week” said Penny.

She also wrote him a cheque for $600 to take care of any expenses throughout the week. It was more money that Barry had in his life, he was college freshman after all.

Penny pulled Barry towards her, french kissing him. “You really do turn me on with that bald head” she said.

Barry headed out the door, looking forward to next week.


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