Allen had only been with two women, including Lindie.
His first sexual experience occurred two years ago with a nineteen year-old local college freshman named Jackie. He was a year younger than her, but several years behind in experience. From the very beginning, she made a point of teasing him.
Short skirts without panties.
Tight t-shirts without a bra.
Pigtails and ponytails.
Sucking on lollipops in class.
Being sent home by the dean was almost a common occurrence for Jackie. Her friends thought making other people treat her like a child was all part of the act. To the casual observer, she hardly looked old enough to drive.
She would make the front of his pants wet with pre-cum within minutes of being in the same room with him.
Jackie switched schools from State to a community college only a few months before finishing her first year. One of her professors found a bag of marijuana in her purse. She claimed that the dean was setting her up.
Jackie was known to drink, but she didn't smoke. It didn't matter, though. The dean had a solid case and Jackie's reputation left her no room to argue.
Allen was devastated. She had been the object of his fantasies for several months. He never had the nerve to ask her out. He just added it to the many missed opportunities of his life.
It wasn't until a late-summer pool party at a friend's house that he literally ran into her again.
Jackie was obviously drunk.
He was immediately aroused at the sight of her wearing a tiny string bikini. Unfortunately, his excitement was no secret to anyone in or around the pool, even in the dark, as Allen's throbbing member found its way out one of the legs of his swim trunks.
It wasn't the biggest cock Jackie had seen, but she found it very attractive and thought it would look even better sliding in and out of her hairless, wet pussy.
She threw him a towel, which he quickly wrapped around his waist. She then led him inside to one of the bathrooms.
"I hope that means you're in the mood to fuck, because I sure as hell am!" Jackie exclaimed as she locked the door and untied her string bikini. She pulled the towel from his waist and pulled down his shorts. As she bent down to pull his shorts from around his ankles, he unexpectedly shot several streams of come on her face, some landing in her eyes and some in her mouth.
Every other cock that had been in her face was strictly forbidden to come in her mouth, so the taste was foreign to Jackie. After this little fortunate accident, though, she made a point of trying to swallow every load that came her way – at least once. She soon realized that diet sometimes made a difference, and some boys tasted better than others. Whatever Allen had been eating, she hoped he would eat more as she scooped some of the come from her cheek to her mouth.
"Are you a virgin or something?" Jackie asked.
"Something like that," Allen admitted.
"Well, maybe you can try eating my pussy. If your dick gets hard again before anyone knocks on the door, I'll let you fuck me, okay?" Jackie asked as if brokering a deal.
Allen wasn't very good. His limited porn collection didn't explain the mechanics, his friends weren't at all helpful, and he wasn't imaginative enough to position himself properly in the tiny bathroom.
Here he was, on his knees before the girl he had wanted for almost a year, and he didn't know what to do. He had prematurely ejaculated on her face before they had even started, and she was still willing to go all the way with him. He prayed he wouldn't screw this up.
She backed up and lifted her bottom onto the sink of the vanity and positioned her feet on a toilet paper dispenser and a towel rack. Allen moved his face closer and inhaled her scent deeply. It wasn't what he expected, but it wasn't foul, either. He opened his mouth and stuck out his tongue, parting her wet labia. Wetness covered his chin as he slipped and smashed his face into her pussy. Jackie winced partially in pain, partially in humor, but mostly in frustration.
"I'm so sorry. Maybe I should-" Allen was cut off.
"Fuck me. Just put it inside me. I'll help you with the rest." Jackie instructed.
Her eyes widened as he stood up and his throbbing dick, now at full girth, jutted out in front of him.
"You're gonna make some girl real happy some day." Jackie said as she placed her ankles behind his thighs. She pulled him closer until the head of his cock was at her wet, open slit.
She pulled a little more and he was inside her. It was unlike anything he had imagined. He felt her ankles dig into his thighs and he moved in closer until his full length was inside her. The head of his cock pressed against her cervix.
"That's a nice fit, isn't it?" Jackie smiled as she pulled his face up to hers and kissed him deeply.
Allen couldn't answer as he was on the verge of another orgasm.
"Already?" Jackie exclaimed.
There was a knock on the door, then several more knocks.
Jackie pushed Allen back and his cock unceremoniously flopped out of her pussy. She grabbed a handful of toilet paper and wiped the come running down her legs, forgetting all about the two or three streaks of come on her face. Allen quickly pulled on his shorts, and the smell of Jackie's cum-filled pussy remained with him the rest of the night. Jackie, in her haste, somehow managed to put her bikini bottoms on backwards.
"I'm not finished with you, Allen!" Jackie said with a grin as she unlocked the bathroom door.
"You'll need to come over to my place when there'll be less interruptions."
Allen nodded and quickly left the bathroom. Minutes later, when it looked like everyone was preoccupied, he left the party.
He had heard rumors that she went back to the bathroom three or four times with three or four different guys, but he still found it difficult to turn her down when she called him a few weeks later.
It was late summer and her parents were visiting friends across town. She asked if he'd like to learn how to please a girl, and Allen practically ejaculated at the thought.
He made a point of not being early. He didn't want to appear too eager, but whom was he kidding?
When Jackie answered the door, she was wearing a very thin summer dress – something she normally wore over a bikini – except this time, she wasn't wearing anything underneath. Her shiny black hair was up in a ponytail and she wore cute little flowered flip-flops that looked like they were meant for a girl half her age. Her face, however, had all the sex appeal and confidence of a young woman who knows what she wants.
Allen could feel the wetness in his briefs spreading.
She hurried him inside and told him to go downstairs into the basement. He could barely see where he was going and almost fell down the stairs. Jackie had lit several candles at the far corners of the room, but they cast very little light on the table and futon in the middle.
"Allen, sit on the futon" Jackie instructed.
Allen did as he was told, trying to conceal the wet spot forming at the end of his semi-erection.
Jackie sat on the table in front of him and spread her legs. She placed her feet on the futon and slowly raised her summer dress as if putting on a show for Allen. Her small frame, small tits, and hairless pussy made Jackie seem years younger than she really was. Allen dropped to his knees between the futon and the table, being careful not to slip and smash his face into her pussy this time.
"Kiss me first," Jackie said. Allen bent down. "On the mouth!"
Allen sat back up and kissed her as he had always wanted. He held her close as their tongues swirled around, and for a moment, Jackie thought she knew what it was like to be loved.
"Okay, that's enough!" Jackie said as she caught her breath. "Do you want to learn how to eat pussy or not?" Allen nodded, licking his lips.
She appreciated his enthusiasm. She didn't want to tell him he had almost made her orgasm just by kissing her. She didn't know how long she was going to last once he put his tongue to work down there.
"Start slowly. Kiss my thighs and legs, then work back up to my pussy." Jackie instructed.
Allen immediately did as he was told.
"Good. Now, do that again. But don't be in a hurry, unless I tell you to." Jackie sighed as Allen softly kissed her calves and inner thighs.
"Now, lick around my pussy. Just the outside, for now."
Allen did as he was told. As he exhaled on her clit and lips, she caught a chill and her nipples instantly hardened.
"French kiss my pussy. Put your tongue inside and swirl it around, then come back to my clit."
Jackie began breathing more deeply, and found it difficult to talk.
"Now, uhhh, put two fingers inside me and press upward like you're trying to lift me, uhhh, up."
Allen did as he was told. She began to gyrate her hips around his hand and she guided his third finger into her slit. She began to moan as Allen began to push his three fingers inside her more deliberately. She bucked against his hand, and in doing so, caused Allen to accidentally slip his pinky finger into her asshole.
"Oh shit!" Jackie called out. "Fuck, yeah!"
The look on Jackie's face was a mixture of incredible pain and intense pleasure as she held onto her orgasm for as long as she could.
"Get on top of me, quick!" Jackie cried out.
Allen pulled down his pants and Jackie immediately reached for his wet cock.
"You can come inside me. I'm on the pill." Jackie explained.
It was a good thing, because as soon as Allen was inside her, his orgasm was immediate.
"Oh fuck, that felt good!" Jackie sighed.
"I'm sorry I didn't last very long." Allen said, embarrassed.
"That's okay. I came! You just have to do it some more, and you'll last longer." Jackie said as she sat up and pushed Allen back onto the futon.
Jackie stood in front of him and lifted her sundress over her head. She turned to show off her round ass and firm legs, moving her head to make her ponytail sway.
"Do you like my body?" Jackie asked, knowing from his returning erection that he did.
"How many times do you think you can fuck me before my parents get home?" Jackie asked.
Allen almost came again just thinking about it. He never imagined Jackie or any other girl ever asking him that question.
She knelt between his legs and engulfed his half-erect cock. The taste of her pussy mixed with his come made her mouth water. She didn't want him to come in her mouth, even though his come was surprisingly palatable. She wanted his cock in her pussy, and maybe even in her ass if he was up to it.
Something about being his first lay and personal sex trainer made Jackie unbelievably wet.
She straddled Allen, pushing him down on his back, and guided his thick cock into her pussy again. This time, she was careful not to show too much excitement.
She raised and lowered her ass slowly, as if trying to feel every vein in his cock with her pussy. Within two minutes, he was filling her with come, again.
"Okay, a little better." Jackie said, somewhat frustrated.
She knelt between his legs again, and coaxed his sophomoric cock back to erection.
This was one form of remedial education that Allen couldn't help but enjoy.
Over the next two hours, Allen filled Jackie's cunt at least ten times, and she wondered how she was going to explain all the come stains on the carpet and futon. He had licked her pussy three more times, bringing her to orgasm easily. Jackie was a good teacher, apparently.
She knew her parents would be home within the hour and decided to push the envelope while she still had time.
She wanted to see if he was interested in her ass.
Some guys weren't, but her last boyfriend, Bill, was obsessed with it.
She liked having her asshole fingered while a guy went down on her, and even thought about letting some guys fuck her in the butt. Bill's cock was too big for her tiny asshole, though, no matter how much they both lubed.
Even though she really wanted to feel Bill's cock in her ass, she thought it was physically impossible. Every time they tried, the pain was too severe, and her asshole just wouldn't stretch enough to accommodate him. That didn't keep Bill from trying, though. He knew she liked his fingers in her ass, and thought if he forced three of his large fingers inside her anus, she would be willing to take in his huge cock. She repeatedly said 'no' and he repeatedly whined about it until she took his cock in her pussy or mouth and fucked him hard enough to satisfy him. She even let him slap her around in a playful, kinky way, just to keep him from tearing apart her asshole.
She thought he was being stubborn, and he thought she was holding out. Some of the other boys she had been with bragged about what a good ass-fuck she was, but she swore to Bill that she had never had anal sex with anyone.
Even though their sexual relationship was great otherwise, Bill wouldn't leave well enough alone. After he hit her too hard to be considered playful, she couldn't hide the bruises anymore. Her parents called the police, putting a restraining order on Bill, and then forced her to end the relationship.
Jackie looked hard at the shape of Allen's handsome cock and licked her glossy lips.
It was smaller than Bill's, but still a respectable size. It might hurt a little, but Allen was more patient and gentle, and if she couldn't handle it, she knew he would listen if she told him to stop. Besides, she didn't want him to be the only one losing a cherry today.
"Do you want to lick my butt hole?" Jackie asked bluntly.
"Do you want me to?" Allen asked, sheepishly. He knew she liked having his pinky finger in her asshole, even though it was by accident. But he never considered intentionally putting his tongue in her ass.
"Yes," she answered, "if you think you might like it."
Allen sat up as Jackie stood at the edge of the futon and turned around. She bent over, spreading her legs, and pulling her cheeks apart.
"I'm clean. Trust me." Jackie said as she felt Allen's breath on her asshole. Her ass cheeks became covered in goose bumps.
He remembered what she taught him about eating her pussy and tried the same approach to tonguing her asshole.
It had an identical effect. She had him spit on her anus, and then he slid a finger inside while kissing her ass cheeks. He alternated between his finger and his tongue until she made him push two fingers inside her tight, pretty pink hole.
Jackie was almost embarrassed that she was so quickly on the verge of anal orgasm.
After only a few minutes, Jackie turned around and pushed Allen back onto the futon.
She pulled a small tube of KY from the drawer of the table, and rubbed a large amount on Allen's rigid cock.
She stepped onto the futon, being careful not to hit her head on the ceiling. She then turned around and squatted, guiding the tip of Allen's glistening cock to her tight sphincter.
"This will be a first for me too, Allen." Jackie said as she looked over her shoulder.
She lowered herself until the head of his slick cock popped into her anus, and then took a deep breath.
The pain was immediate, but short-lived, and Jackie lowered herself a little further.
"So far, so good, huh?" She asked.
Allen was speechless. He was doing everything he could to not come and end the experience prematurely.
Jackie lowered herself further, exhaling as more of his cock disappeared inside her.
To Allen, the sight of Jackie's back and ponytail was a thing of beauty. The view of her round ass and full, toned legs was a work of art.
She began to move up and down on his shaft and quickly brought a hand to her clit. Her other hand groped at her small tits as she carefully maintained her balance and continued sliding his dick in and out of her ass.
Allen felt Jackie's asshole tighten around his shaft as she brought herself to orgasm. It was almost painful at the onset, but as her sphincter relaxed, the pressure in his loins began to build. She sat fully on his dick, pushing it deep into her bowels.
She remained motionless, but he could still feel the spasms deep within her. Her head fell back and she felt his warm come fill her asshole, making her sphincter tighten again.
She sat on his lap, motionless, for a moment. They both quietly reflected on what had just happened, and Allen's dick began to harden inside her.
"Okay, one more time, but that's it for today." Jackie looked over her shoulder and smiled.
"I don't want to get too sore down there."
She raised herself slightly and swung her legs around so she was straddling his lap, facing him. He kissed her hard and she pushed herself down onto his lap, forcing his cock inside her as far as it could go. The head of his cock squished deeper in her bowels as it became further lubricated with his previous orgasm.
This time it was Jackie's turn to orgasm quickly.
"Oh fuck! I never knew it could feel so good," Jackie sighed and covered Allen's face with kisses. A few minutes later, Jackie slowly sat up.
"It might be a little gross down there when I get off of you." Jackie warned.
"It's okay. It comes with the territory. Do you have a shower down here?" Allen asked.
"No, but I can get a couple of warm washcloths, if that's okay?" Jackie answered.
"Sounds great." Allen smiled, proud of being able to make this sweet, gorgeous, reputed slut sexually satisfied.
The sound of slow, loud clapping filled the room.
Barely visible at first, Bill stepped out of the shadows.
He was completely naked, his thick, semi-erect, nine-inch cock bouncing before him.
"Great show. Congratulations on finally getting your asshole cherry popped, cunt!" Bill smiled maniacally.
Jackie quickly sat up and reached for her sundress. The smell of sex filled the room.
"How the hell did you get in here?" Jackie asked.
"You gave me a key, remember?" Bill laughed and began stroking his rigid, fat cock.
"Well, you shouldn't be here. We broke up, Bill. You need to go." Jackie said, practically crying. Allen sat up, not sure what Bill was doing there, either.
Bill was over six feet tall, 220 pounds of muscle, and had a bad temper. Allen was no match for him, and he could see the situation was getting worse by the second. He just didn't know what to do about it.
"My parents will be home any minute, Bill. You really need to go. They put a restraining order on you, remember? You'll end up in jail if they find you here." Jackie pleaded.
"Well then, I guess I better make this worth it!" Bill said as he charged at Jackie.
Allen stood up, and tried to stand between them, but one swing of Bill's fist sent Allen falling to the floor, barely able to breath. Blood filled Allen's mouth as he began to lose consciousness.
Jackie turned to run up the stairs, but Bill was faster.
"I don't think so!" Bill said as he grabbed Jackie around the waist and pulled her against his lap. He yanked the sundress from her hands and tossed it aside.
"What's it gonna be? Your pussy... or your maybe your ass, this time? Looks like it's stretched some since the last time we tried, huh baby?"
"Ouch! Bill, you're hurting me!" Jackie cried. Allen felt helpless in his state of delirium. He watched as Bill held her close to his chest, lifting her legs, and shoving his large cock into her pussy. Jackie kicked her legs violently, sending her flip-flops flying across the room. Bill ignored her movements as he forced her legs apart and thrust deeper from behind.
"Oh yeah! That's better. Just the way you like it, remember?" Bill asked.
Allen's head was pounding. He didn't even have a chance to pull up his pants when Bill hit him. He tried to move as little as possible while he looked around the room.
Allen managed to catch a glimpse of an old, wooden baseball bat less than five feet away.