The Sorority Pledge

The Sorority Pledge

Sandy had a boyfriend, but she still hung out with her childhood friend Tim. They grew up as next door neighbors and started school in kindergarten together. Tim had a crush on her, but he never acted on it. She liked the macho types, the athletes. He was anything but that.

Sandy never thought twice about dressing up in front of Tim and even stripping naked in front of him. She just knew he wouldn't do anything. When they were in junior high together, she would sometimes ask him about what bra or panties or other clothing she should wear, and he told her what he thought

She would joke about having a girlfriend with such good taste. Then, she would start teasing him about wearing her bra and panties. He would blush with embarrassment, but then it happened. He started wearing lingerie under his clothes for her.

This continued through high school, and she even dressed him in her old cheerleader’s outfit, which fit his slender frame. She did his makeup and took pictures, but it was all in fun. She started referring to him as Tina.

While guys she was dating might get jealous of Sandy fussing over another boy the way she did, none of them ever gave it a second thought with Tim. Tim was very submissive towards them and would run errands for them or even do their homework. Nobody ever thought to bully Tim when Sandy was dating one of the big guys. If they did, they learned a hard lesson.

In college, Sandy was about to pledge a sorority, and she was nervous as she picked out an outfit. She wore her pink thong panties and matching bra as she held a pink hello kitty top against her while looking in the mirror. "Do you think this will work with that pink skirt we bought at the mall last week?"

Tim stirred in his underwear and blushed. He admired her perfect figure. She had the cutest ass, but her breasts were even more amazing as they were almost DD. Her long blonde hair went down past her bra strap. She had the cutest dimples when she smiled. "I think so, " he replied. "But you look amazing in anything."

She kissed him on the cheek. "You're the best girlfriend a girl can have."

His cock, all of about four inches, was hard, and he walked away from her towards the window to hide it. "Stop it, Sandy. You know I'm not a girl."

She laughed. "That's not what they said at the Alpha party last week. You looked amazing in my black dress."

Why wouldn't his erection go away? Why couldn't he tell her how much he loved her? "Sandy, you know I only did that so you wouldn't go to the party alone."

"That's my Tina, always so helpful. You know, I think Brad has a thing for you. After you helped him pass that economics class, he was able to get into college. He's here, you know?"

He blushed. "Sandy, please, I did it for you."

She looked at him for a moment. "Why have you never had a girlfriend? Is there something you want to tell me? You can tell me anything, sweetie."

Why couldn't he tell her how he felt? "I'm not gay, Sandy. I'm just... You wouldn't understand."

She smiled. She knew how Tim felt, but she was waiting to hear it from him first. Through all the break ups, Tim was always the one there helping her pick up the pieces. She didn't know what she would do without him.

She went to the closet. "Never mind that. We have to pick you out something to wear."

"Sandy, wait. I can't go. Last week was one thing..."

"Oh shush, you'll be fine, " she said as she threw a black skirt and a pink blouse that said princess on it in glitter on the bed. "Let your hair down, sweetie. We need to do something with it."

He shook his head. "Sandy, I don't even know what this deal is all about. I'm not even sure a guy can go to a sorority pledge party."

She giggled. "Well, you won't exactly be a guy."

"But..."

"And they said we could bring somebody with us. Strip, girlfriend. I think I have another pink bra and panties that will work for you if you don't mind panties with cock sucker written on them."

"Sandy."

"Oh, stop it, " she threw him the panties and his face went red when he saw the word cock sucker written on the back in black glitter. "You never know, they may accept a sissy in the sorority."

"Sandy, I'm not a sissy."

"Of course, you're not, " she said almost sarcastically. "But you do look cute in a skirt, and you are a natural."

He stared at her with his mouth open.

"It helps that you have a good teacher like me, " she added with a smile.

"Sandy, I can't do this."

She pouted as she walked over to him, glancing at his small erect penis and then his face. "Tina, please. I need this. Anybody who is anybody is a Pi girl. Don't you want this for me?"

His heart melted. "I guess so."

She hugged him. "Oh, thank you Tina. Thank you. Thank you so much. You're the best."

After an hour fussing over Tim's hair and makeup and making sure his outfit was just right, the two went to an unmarked building on the edge of the campus.

A short black haired girl stood at the door and smiled when she saw the two approach. "Sandy, " she said as she kissed her on the mouth. "Just so you know, this is a formality. All girls have to go through this before joining, but you are definitely in."

She looked Tina up and down. He looked quite passable in his pink top and black skirt. He wore a pair of cute pink sandals, and Sandy had hastily painted his toe nails a bright shade of pink. She smirked. "Is this the one you told us about?"

She nodded. "Uh huh. Tina is very smart. She had a 4.0 average in high school, and I just know she would be a big help to all the sisters here."

The girl giggled. "Well, we'll just have to see if she can handle the initiation."

Initiation? Tim wondered what Sandy had gotten him into. He started to get nervous. "Sandy, I..."

She turned around. "Shush. Just follow me, do what I do and you'll be fine."

They entered the building that had a lot of furniture in the big front room. There was a hallway beyond. "Down here ladies, " came a female voice.

They walked down the hall into a room that was empty. In the middle of the room, there was a makeshift wall with some holes in it, and a brunette was on her knees in front of one of the holes. Tim did a double take when he saw the woman was sucking a cock through the hole. It was the biggest cock Tim had ever seen.

A blonde lady stood behind the two. "April just got started, but there's plenty to go around for all the pledges. Remember, your enthusiasm will go a long way towards your acceptance here."

Another cock appeared through a hole. Sandy licked her lips. "Sounds good to me, Jenny."

"Sandy, I can't..."

"Is there a problem ladies?" Jenny looked at Tim.

Sandy took Tim's hand and led him to the cock. "Not at all, she's just nervous."

"Okay, well you mustn't keep these boys waiting. They have a big game tomorrow."

Sandy and Tim got down on their knees in front of the cock. "There's nothing to it, sweetie. Here, let me show you."

Tim watched Sandy plant a big kiss on the tip of the cock, leaving a trace of her pink lipstick behind. He was rock hard in his panties as she started licking it and then sucking it. She bobbed slowly up and down on the eight inch cock, humming as she did it.

She pulled up. "You try it, sweetie. It's okay."

He was face to face with the cock when she pushed his head into it. As the cock touched his lips, he opened his mouth as he took it inside. He was shocked and overwhelmed by the experience.

She giggled. "You looked like you needed help."

Her hand was still holding his head on the cock. "Use your tongue sweetie. Don't bite, and keep sucking."

He tried to say stop, but the tip of the cock was tickling his throat and testing his gag reflex. He gave in and started licking and sucking the big cock in his mouth."

Sandy smiled at him. "Good girl. Now, move your head up and down. That's it. When you hum, it gives him pleasure as your tongue goes underneath his shaft. That's it. Oh, Tina, you're a natural."

Tim was in overload as he sucked the cock. Without touching his own cock, he could tell he was leaking. "Okay, let me have some more. Sandy took over and Tim looked over to see April had her skirt hiked up and was taking the cock inside her from behind. Another girl had entered the room and was sucking cock

Sandy snapped him out of it. "Okay, suck him some more sweetie. I think he's ready to pop."

Pop? He started sucking again and could taste something he never tasted before. A little bitter, but not unpleasant.

"Do you want the load, or should I..."

The man came hard inside Tim's mouth, and he dribbled some of it down his chin. That's when Sandy surprised him by kissing him deeply and sharing the load, licking his chin and sharing that in a kiss as well. She returned her attention to the cock, which was still there, draining it the rest of the way.

She kissed Tim again. "See, you are a natural. I was right."

He was on his knees in a daze as Sandy moved over to the other hole to greet a big black cock "I hope you don't mind, but this is too good to pass up. Stay there. Another cock will come."

What had just happened? Tim barely had a chance to think about the cock that just came in his mouth or that wonderful kiss with Sandy before another cock appeared from the wall. It was too late to think anymore. He started sucking it like a greedy little slut.

Stacy stopped briefly. "Go for it Tina. I wish I had known you were a little glory hole slut like me. We could have done this a long time ago."

Jenny stood at the door, nodding approvingly. "Only the girls who truly commit are worthy of becoming Pi girls. April, you're in."

"Thank you, " she replied with a smile as she took cock from behind. "Can I stay a little longer?"

She laughed. "Of course, you can you little slut, but the real action will be out front in about an hour. You'll get all the cock you can handle there."

Sandy surprised Tim by lifting her skirt and taking the big black cock from behind. She looked over at Tim. "Tina, sweetie, you have to try this. All the pledges have to do it."

The other girl at the far end got up and left. "That's it. I'm out."

Jenny shook her head. "Well, not everybody is cut out to be a Pi girl. Are you, Tina? Sandy had good things to say about you, and we'd love to have somebody like you in our group. Even if you are a little sissy, you're still quite attractive."

Tim blushed. What had Sandy gotten him into? Could he go any further? Watching Sandy taking that big black cock had him curious. He wanted to do what she was doing. More than that, he wanted her acceptance.

He hiked up his skirt. Sandy smiled, "I knew you wouldn't let me down. That's why I love you. Oh, God. You have to try black cock, girlfriend. It's the best"

Jenny giggled as she watched. "Hey girls, the sissy is doing it. She wants to be a Pi girl."

Another girl appeared at the door. "Perfect. We need a new t-girl since Abby graduated."

Jenny was watching attentively. "Well, she hasn't done it yet."

"Oh fuck, " said Sandy with a frown. "He popped already."

She moved in front of Tim to encourage him. Tim was pushing against the cock, but it was hurting. "Oh, God. Sandy, I don't know if I can."

She kissed him. "Of course, you can. You're gonna be a Pi girl, just like me. Just think, we'll be roommates too once we join. You and I sharing a room together."

"Roommates, " he said with a smile as the cock slid past his tight opening and he moaned. "Oh God, it hurts."

"You're doing good, baby. Yes, we'll be roommates, and after tonight, we'll share everything. I'll let you eat my pussy, that is if you still want to after having your first taste of cock."

"Oh God, " he cried as the pain scared him just a little bit.

Jenny laughed. "Now you know what we have to go through, Tina. Just take it like a woman. You're gonna have to get used to it if you're gonna be a Pi girl."

Tim felt like the cock was deep inside him. "Oh, no."

Sandy kissed him. "What's wrong sweetie?"

"I didn't put a condom on him."

The girls all laughed. "It's not like you'll get pregnant, sissy. You'll just get to find out how it feels when a man cums inside your ass."

"But..."

"The guys are tested all the time, Tina. Don't worry about it."

As the anonymous man pushed his cock in and out of Tim's ass, he pushed to take it deeper. He had no idea what was coming next, but he was feeling good as he got used to the big cock fucking him. Sandy kept encouraging him and kissing him. He always wanted to kiss her on the lips, but he never dreamed it would be while he had a cock in his ass or after the two had sucked cock together.

It wasn't long before he felt the first spurts of a man's cum shooting inside his ass. He felt a strange sense of happiness and contentment, even though he hadn't cum yet. He was unprepared for what was next as the cock exiting his freshly lubed ass made a popping sound.

Tim was on his knees with cum starting to leak out of his hole as Sandy hugged him and kissed him. "You're a Pi girl now, Tina. And there's something else."

He didn't know if he could handle any more news. "What's that?'

"You remember how I was telling you about how Brad was attracted to you?"

He looked confused. "Yeah, so?"

"You just took his cock in your ass, sweetie. He's the one who took your virginity."

"How do you know?"

"It was arranged that he would be here at this time, " Jenny replied.

"But, how? Isn't this anonymous?"

Jenny grinned. "I'm the sorority president, Tina. I can arrange anything here."

Tim blushed "Oh my God. Does he know?"

They all laughed. "Of course not, silly. This is anonymous. Sandy just wanted you to know how it felt to be fucked by him. How did it feel?"

He said nothing. He was in shock. Sandy looked at him and laughed. "That's about how I felt. It's not just that he's big, he actually knows how to use it. A pity he had to cheat on me."

Jenny turned to leave. "That's it for the initiation. Only two girls couldn't handle it this year. Their loss. The party is in the front room, girls."

Sandy looked at Tim. "Do you mind if we leave early? Tina and I need to talk."

"Not at all. I'm hoping you two pack up and get into your new room as soon as possible. Orientation is next Monday."

Tim looked at Sandy. "Why? Why did you do this?"

A tear fell from Sandy's eye. "Because, once I moved into the sorority, you and I wouldn't be hanging out like we used to, and I didn't want that. I also had to be in this sorority, just like my mom and my older sister."

"But still..."

She put her arms around him. "And because I love you, you little sissy. You've always been so nice to me and put me first, and no man has ever done that for me. And I know you love me. I don't know why you can't say..."

"I love you more, " he said as he kissed her passionately. "I always have. So, why all the sneaky stuff?"

She grinned. "It was the only way to get you in here. You do like the idea being in a sorority with all of these beautiful women, running around the house in lingerie and tending to the needs of all the girls, don't you?"

He nodded. "Oh yes."

"Good. Now that that's settled, let's get back to my room. I need to get packed and so do you. But, before we do that, I want to see if you eat pussy as well as you suck cock."

She took him by the hand and they left together. Tim was on overload. He had said what he always wanted to say to her and she confirmed her feelings. He never thought he'd take cock inside him, but he enjoyed the experience. He wondered what would happen the next time he saw Brad. He wondered what sorority life would be like. He looked forward to finding out.