Becoming A Sissy

chapter 4

The halls were quiet and empty letting Tammy walk uninterrupted to her room. When she arrived Helen was waiting on the couch.

"Well someone looks happy." She said. Tammy started to blush thinking about what happened in the shower.

Tammy started telling Helen the whole story. Tammy felt comfortable talking to her because she was like the big sister she never had.

"Wow! You had your first experience with anal!" Helen exclaimed. "I'm so happy for you. Now wanna do some training?"

"Where's Jeff?" Tammy asked.

"That loser is in his room." Helen answered. "I know this is pretend and all, but you're way too good for him."

"You sound like you dislike him, so why help him?"

"Same reason you are. He's got dirt on me, and I'm gonna get back on him, but I digress. You have the look, voice, and posture of a beautiful woman now all we need is to practice. Jeff said he doesn't want to do any work, so I arranged a date for you."

"Like, in public?!"

"Don't worry. Everyone thinks you're a girl, and it's not like you're actually dating the guy. He's just practice."

"But-"

"Trust me. You'll do fine."

"Oh, alright." Helen helped Tammy pick an outfit. They landed on a crop top, heels, stockings, and a very short skirt. "So where is the date?"

"At the bar just down the street. I'll be there if you need anything, but try to just enjoy yourself." They walked to the bar. Even though Tammy was dressed more scantily than before, she wasn't terrified of being seen thanks to Helen.

When they arrived Helen pointed out Tammy's date and they parted ways. Tammy's date was a tall skinny guy with short dark hair. He looked so familiar to Tammy, but she couldn't put her finger on it.

"Hi. I'm Tammy."

"Martin."

Tammy realized where she recognized him from. They went to highschool together.

"Let's buy some drinks." Martin said

"I don't drink." Tammy was only nineteen.

"C'mon just one."

"Ok." Tammy didn't want Martin to think she was uncool or admit she was underage.

They chatted while waiting for the bartender to serve them.

"I must say. You're the most stunning woman I've ever seen." Martin stated. Tammy couldn't help but blush at the compliment.

"Thanks. Your not half bad yourself." Tammy wasn't lying he was quite the catch.

The bartender gave Martin a beer and Tammy a colorful margarita. She took a sip. It was fruity and a little bit sour. They talked and drank for around half an hour, before Tammy finished her drink. Martin was on his second beer.

"This has been fun, but I should head home." Tammy said.

Martin grabbed Tammy's waist and pulled her in close. "But it was just starting to become fun." He leaned down and started to kiss Tammy's neck.

"I don't know." Tammy was fighting the urge to moan.

"Tell you what, a quick handjob in the bathroom and I'll pay for your drink."

"But I didn't bring any money!" Tammy exclaimed.

"So looks like it's your only option."

Tammy didn't want to jerk some guy off, but she was backed into a corner. "Fine. Just hurry up." She said. Martin led her into one of the men's stalls. He gently pushed her to her knees, and let his dick out.

His dick was huge compared to Tammy's. She put one hand around it, and started to jerk him off. Martin's dick let out a musky oder which was somewhat revolting.

"Good slut." Martin said. Tammy couldn't speak out of embarrassment. Martin's dick started to leak precum.

"You know what? You've done such a great job. Stop jerking and give daddy a big smile." Martin said.

Tammy let go, and gave Martin her best smile she could manage. Martin took over the jerking off, and soon cum came shooting out and landed on Tammy's unsuspecting face. The thick load started to run down her face into her hair and clothes.

"OMG! That wasn't part of the deal you dick!" Tammy screamed. Martin paid her no attention and just calmly left. Tammy washed up in the sink and left to find Helen. At first glance she was nowhere to be found, but after some intense searching she spotted her under a table giving a guy head. She motioned for Tammy to come, so Tammy crawled over to her.

Helen gasped for air and asked, "I'm exhausted. Do me a huge favor and finish him off for me. I'll explain later." Tammy didn't want Helen to injure herself, so she agreed. Helen held Tammy's hair out of the way, as Tammy started sucking the dick's head.

"Good. Now just suck and slowly move up and down the cock. Don't let your teeth ever touch." Tammy felt comfortable with Helen giving her support and advice. Tammy started to pick up the speed. "Yes just like that. Now try to go as deep as you can and hold." Tammy got her lips all the way to the base of the cock. Tears started to form in her eyes.

"Now release." Tammy released the cock and started gasping for air. "Don't take to long" Tammy went back to sucking. She felt the man's legs start to shake, indicating he was about to cum. She started to pull out, but Helen pushed her head forwards. Cum spewed out of the dick. Tammy felt the creamy load slide down her throat. Helen released her grip, and Tammy sprung back to catch her breath.

"So how's the taste." Helen jokingly asked.

"Not as bad as I thought." Tammy answered.

"C'mon let's get out of here." Helen said. The man stuck some money under the table. Helen grabbed it and they walked back to Tammy's apartment chatting the whole way.

"Helen? These recent adventures have gotten me really horny. Could you release my dick, so I can stop feeling so pent up?" Tammy asked.

"Ohh sweetie. I understand. Real dicks would make any girl horny, but sissies don't jerk their little clitties. If you're horny you'll cum the sissy way with a dildo."

"But I'm not gonna cum from fucking my ass. That's weird."

"I'm sure you would have said the same thing about giving a stranger a blowjob, but you did great."

"I guess."

"How about you come to my apartment, and I'll help you relieve yourself."

"Really?"

"Of course. What are big sister's for?"