Jimmy's Dilemma

Jimmy marveled again at his luck. Angela, who had been the hottest cheerleader in his high school and was now one of the hottest chicks at his college, wanted him in her bedroom? It seemed impossible. Yet, here she was, opening the door of her apartment. He flashed back to yesterday, when she stopped him in the hallway at school.

Angela was wearing a short, pleated skirt just like the ones she used to wear as a cheerleader. Her top was a thin white blouse, tied off just above the skirt so that a strip of her perfect abs peeked out between them. She grabbed him by the arm as he passed by, and asked if he had a second to talk. Jimmy didn't even know she knew his name.

"Jimmy, how are you? You remember me, right? We both went to Newton High." Jimmy was so nervous he just gulped and nodded his head, mumbling a vague "...'course."

Angela smiled, her perfect lips parting and white teeth flashing as she giggled. Her full breasts jiggled with the giggles, and Jimmy felt himself getting hard. He held his backpack in front of him, to hide his bulging erection as Angela continued.

"Yeah, well...listen I want to ask you a favor." Her eyes suddenly stared straight into him and she bit her bottom lip seductively. Shit! Jimmy felt like he was about to cum in his pants. He stuttered as he replied "sure, what is it?"

"Umm, you know my boyfriend Eric, right?" Jimmy nodded. Everyone on campus knew Eric, start quarterback on the football team. "He can't know about this" Angela continued "but, well, I have a fantasy that I want to act out and Eric isn't into it. I always had a crush on you in high school, but you had a girlfriend...now here we are, away from home in the same college. And I thought, maybe you could be the one to help me get this out of my head."

Jimmy glanced around self consciously, looking for Eric. Angela had a crush on him? What the fuck? She was out of his league and he knew it. Jimmy had always been described as cute, but at 5'5" and slim as he was, that cuteness had always been far from the manly image of a jock. He wore his blond hair a little long, and it gave him what he hoped was a rocker look but his girlfriend Missy told him he just looked sweet. Now, here was Angela the hottest cheerleader on the team telling him she had a secret crush.

"Fantasy? What kind of fantasy?" Jimmy said.

Angela smiled shyly, and looked down, which made him glad his backpack was strategically placed. "Are you kinky, Jimmy?"

She explained to him that she had a fantasy in her head, of making love to a transsexual girl. The idea of "luscious lips, gorgeous boobs, and a hard cock" made her instantly wet, she said. She had tried to get Eric to play the part for her, but he wouldn't go for it. Said it was "too gay". Angela explained to Jimmy that lately she couldn't think about anything else.

"It would just be a one time thing" she said. "And Eric can't find out. He would break up with me, and beat the shit out of you."

Jimmy shivered in fear at the thought of Eric beating him up, and his cock started to soften in his pants. But what Angela said next brought him right back to attention.

"I understand if you don't want to be with me. But I promise if you do it will be the wildest afternoon of your life." As she spoke, Angela stepped closer to him, pressing near until he could feel her breath on his cheek. He said yes immediately, and she gave him her address and instructions for the next day.

Now, here he was at the door of her apartment. Angela had been very clear that he had to show up on time, and he had. When she opened the door, Jimmy immediately became hard. She was wearing a robe, loosely tied and hanging open seductively so that he could see underneath. All he saw was a skimpy pair of red panties and a flash of matching bra. Everything else was smooth skin.

"Hey Jimmy" Angela smiled, standing there and looking him up and down. Her eyes stopped on his bulge, and she giggled. "Don't blow it too early baby."

He followed her into the living room of the apartment as she turned, mesmerized by her ass under the silky fabric of the robe. She strode straight into a bedroom, turned and told him to get naked. Jimmy felt self conscious as he started to strip off his jeans and tee shirt. This girl was way out of his league!

As he finished stripping, Angela walked to the dresser and brought back a bottle of water and held out her other hand, palm up. There was a small blue pill in her palm. Jimmy looked at the pill and then at her.

"I don't need that" he mumbled, a little ashamed that his nervousness had softened his cock.

"I know you don't need it, baby. But I want it. I want you to be rock hard for me all night."

Jimmy immediately reached for the pill and the bottle, swallowing it down. Angela smiled again, her eyes shining mischievously. "Good. Now we can get you ready."

She turned and began opening dresser drawers. Out came makeup, lipstick, and a bag. Angela told Jimmy that her fantasy was to fuck a sexy trans girl, and he wasn't that yet.

Jimmy felt butterflies in his stomach, but if this was what it took to spend a night with Angela it was totally worth it. Besides, nobody else was here and she would be the only one to know.

Angela had him sit on the bed next to her, and got to work. She put makeup on his face, lipstick on his lips (which for some reason made him hard again, and she giggled). Finally, she opened the bag that sat next to her and pulled out two realistic looking silicone breasts. Jimmy stood up and backed away, shaking his head.

"No way! I can't have tits!" he said.

Angela stood, and walked over to him, placing her hands on his bare chest and lightly pinching his nipples. Jimmy was rock hard and dripping precum. "Baby, I told you my fantasy was kinky and that it involved you playing the part of a transsexual. I want to suck on those tits while you fuck me." As she said this, Angela reached down and lightly stroked his cock. Jimmy thought he would explode.

"Are you going to let me have fun?" Angela whispered in his ear, "Or do you want to get the fuck out of my house?" As she said this, her voice became stern and she pulled away. Jimmy answered immediately, "Okay, put them on me."

She smiled wickedly, and headed to her nightstand. From the top drawer, Angela pulled a pair of handcuffs covered in pink fur. Jimmy gulped as she turned back toward him and said "if we are going to fuck, then I want to be in control so I can make it last. Turn around."

The thought of his cock buried in Angela's pussy, as he watched her silky robe sway back and forth around her tits, made him ready to do whatever it took. He turned his back to her and placed his hands behind him, feeling the cuffs close and hearing the clicking of the ratchets. Suddenly, he felt short of breath as he realized he was somewhat at her mercy.

Angela had him sit back on the bed as she applied the breast forms with some type of glue. She then put a bra on him and he caught a glimpse in the mirror. Not bad, he thought. I would totally fuck me.

Angela leaned in and slowly stroked his cock as she nibbled on his right ear. "Mmmm, this is delicious darling. We are going to have so much fun." She giggled, and her breath caught in her throat as if she had just thought of something.

As Angela continued stroking Jimmy's rock hard cock, smearing precum all over the head like lube, there was suddenly the sound of the apartment door slamming and then they heard a male voice calling her name. Angela stiffened, but continued playing with Jimmy's dick as she said "Shit! It's Eric. He is supposed to be at practice!"

Jimmy was in a panic, looking around desperately for somewhere to hide, his fake boobs swinging from side to side as he turned back and forth in his search. If Eric found him here, he would beat the shit out of him Jimmy knew. And not that he would normally have a chance against the buff football player, but handcuffed and naked?

Angela saw Jimmy's panicked face and quickly but quietly pulled him to a door with a large poster of some basketball player covering the front. She opened it and Jimmy saw it was the closet. There were some clothes hanging, and quite a few boxes with just enough room to hide if he knelt facing the door so his legs could slide back under some of the stuff that was stacked there. He did, and Angela quickly closed the door leaving him in the well lit space on his knees with his hands still cuffed behind him and his fake tits pressing lightly against the door.

Somehow he felt more exposed with the light on, but Angela had forgotten to turn it off as she closed the door. Jimmy realized he still had a hard on in spite of the panic he was feeling, and thought it must be the pill she gave him earlier.

He heard the door to the bedroom open, and then Eric's voice "Hey baby, what's up?"

Angela responded "Oh you know, just having some fun. How was practice, lover?"

"Good, but we cut it a little short so I could get here on time like you said."

Jimmy thought he must have heard wrong, but then Angela answered "Mmmmm, you must be really excited since you know I have a surprise for you."

Eric chuckled deeply, and there was the sound of a zipper opening. " I think I can guess what my surprise is" he said.

Angela giggled, then said "I doubt it, but it is perfect for a horny bastard like you. During the last game, I made a bet with a cheerleader from the other team. We agreed that whoever's team lost, they would have to give a blowjob to the quarterback of the winning team."

Eric smiled. "Seriously? Wow, you are a kinky girl."

"You have no idea" Angela said. "Anyway, as you know we won. And I brought that bitch here to pay her debt."

Jimmy wondered where this whole thing was going, but he was starting to not like it. He heard Angela walk toward the closet door as she said "Remember when you put a gloryhole in my door so we could act out your fantasy?"

There was the sound of the poster moving and tape being pulled off as she said this. That is when Jimmy noticed the hole in the door, right in front of his face, and a small view of Angela's panties became visible. Jimmy panicked again, trying desperately to get his face away from the door. He wanted to run screaming from the place, but couldn't open the door and didn't want to because Eric would find him.

"Well, she was ashamed of taking the bet and doesn't want you to see her, but she is going to pay me."

Suddenly, the image of Angela's panties was replaced with Eric's half-hard cock. It must have been 8 inches already, and it wasn't fully hard. Jimmy could see Angela's hand wrap around it and begin stroking, leading him to the gloryhole. Fuck! There was no way he could suck a cock. As the head of Eric's penis came through the gloryhole, Jimmy heard Angela's voice again. This time, she was speaking to him as if he was the cheerleading slut who lost a bet.

"Open up bitch! Are you going to suck this cock or should I open the door and let your bitch ass run home?"

Jimmy felt like he wasn't in control of his own body. He felt disassociated as the huge cockhead came through the gloryhole, followed by the meaty shaft. The head, covered in slimy pre-cum from Angela's stroking, bumped against Jimmy's lips as they parted. It kept coming forward, the shaft sliding over his tongue until Eric's cock lodged against the back of Jimmy's throat.

He heard Angela giggle and Eric chuckle, then he heard "get to work bitch!". Mindlessly, Jimmy began sucking cock, sliding his lips up and down the shaft as it became slick with his saliva and Eric's flowing precum. He didn't want to swallow any of the filth oozing from the head of Eric's dick and so within a few minutes long ropes of spit and precum were drooling from Jimmy's painted lips and coating his breasts as he bobbed his head dutifully.

Soon, he could feel Eric's cock begin to grow in his mouth and then he heard Angela "Okay slut, my baby is about to cum in your mouth. Be a good bitch and swallow every drop, or I am going to drag you out here and let him fuck your ass." She laughed as she said it, and Jimmy knew she was serious.

His mind was screaming and everything seemed to move in slow motion, even though his heart raced. Was he really on his knees, sucking cock for the school quarterback? Was he actually about to swallow a load of semen, like one of the sluts he would masturbate to on porn sites? As Eric pulled his cock back to let the head rest just inside Jimmy's lips, he knew the answer.

Pulsing powerfully, jets of cum began filling Jimmy's mouth. He desperately didn't want to swallow, but realized he had no choice unless he wanted to risk Angela opening the door for Eric to see. And so he let the thick, hot slime coat his throat as it kept coming. It took three gulps before Eric was done using Jimmy's mouth as his personal cum dump. Jimmy heard Angela moaning softly and realized it was from excitement. Evil fucking bitch! Then she spoke up again.

"Lick his cock clean, bitch." Jimmy bent his head to this next humiliation, sucking the coating of cum off of Eric's dick until it was shiny and clean. Eric pulled his softening shaft from the gloryhole, and Jimmy heard them talking again as he realized how his knees were sore and his jaw ached.

"Mmmm. Did my slut do a good job, baby?" Angela cooed in Eric's ear as he tucked his cock away.

"Yeah, she isn't bad for an amateur" Eric replied. They both laughed, and then Eric said "Hey, I should get Bubba home. He's gonna be pissed that he waited in the car all this time."

"Bubba is with you?" Angela sounded surprised. Bubba Johnson was one of linebackers for the team.

"Yeah, he didn't have a ride home after practice today so I told him I would take him after I stopped by here."

Angela's breathing quickened as she made the offer "Well, why don't you invite him in for a turn at this bitch before you guys go?" Jimmy began panicking again. She wouldn't really do that, would she? Offer him up for a turn, as if he was some kind of toy? Suddenly he realized that is exactly what she was doing.

Eric chuckled "Really? Would she do that?"

Angela said "She doesn't have a choice. I own this slut."

"Okay, let me tell him." Eric headed out the door.

As soon as the door shut, Jimmy called out to Angela through the gloryhole "Angela! What the fuck is going on? You need to let me out of here right now!"

He heard her laughter and suddenly saw her face as she knelt on the other side of the hole. "Why would I do that, when we're having so much fun?" She smiled cruelly at him.

Before he could speak, she continued "Now, in just a minute, Bubba is going to walk through that door. When he does, I am going to bring him in here and feed you his cock. And you WILL suck it like a slut, is that clear?"

"Fuck you! No way am I doing that again."

"No? Okay, then we open the door for Eric and Bubba to find out who just gave a sweet blowjob..."

Jimmy realized with a sinking feeling that he was fucked. If he refused, the two football players were about to find out who was really in the closet and find him kneeling there naked, handcuffed, with Eric's fresh cum drooling down his chin. He hung his head and Angela laughed softly at him.

"Good girl" she said as she closed the door.

Less than 10 seconds later, Jimmy heard the front door open and Angela giggled excitedly. "Bubba, baby, I can see Eric told you about the surprise I have for you."

She was already positioning him in front of Jimmy's gloryhole, and as she unzipped his jeans a monster cock sprung out. Jimmy stared through his tiny window and saw that Bubba was dripping a steady stream of precum from the head of his massive erection. He stepped closer to the door as Angela stroked his shaft and aimed the head at the gloryhole.

"Now Bubba, you tell me if this bitch does a good job for you baby. She promised to give you the best blowjob you ever had and to swallow every drop of cum. If she doesn't, then we will just keep her sucking cock until she gets better."

The huge head of Bubba's cock filled the opening in front of Jimmy's face and then popped through, glistening and slick with precum. Jimmy leaned forward and opened his mouth wide to swallow the monster, letting it slide over his tongue. His nostrils filled with the musky scent of Bubba's cock and balls as Angela urged his tormentor to "make the slut work".

Bubba stopped thrusting and instead made Jimmy bob his head back and forth, taking the dick deep in his mouth even though that only took care of about half of Bubba's length. Swallowing as much as he could, Jimmy felt his tongue and lips get coated with a thick slime of spit and precum which began drooling from the sides of his mouth.

"Ready cocksucker?" Angela called from the other side of the door "Your customer is about to blow his load, so make sure you swallow like a good girl."

Jimmy moaned softly in humiliation as he continued sucking slavishly at the giant black cock, knowing that he was about to swallow cum for the second time and there was nothing he could do about it. He felt Bubba's cockhead swell until it filled his mouth, and then suddenly sperm was flooding over his tongue and rushing in hot jets to the back of his throat!

Jimmy gulped down the thick blast of semen, but there was more coming. It seemed like a never- ending stream as blast after blast filled his mouth. Jimmy kept choking down the disgusting slime, until finally it subsided. Angela didn't have to tell him what was next. A tear rolled down Jimmy's cheek and mixed with the cum dripping from his chin as he bent his head and began sucking Bubba's dick clean...