High School Sweethearts Pt. 01

Andi Jessen and Jack Nelson had started dating their senior year of high school, and as so many high school sweethearts do had elected to go to the same college. Jack was three weeks younger than Andi, and on his eighteenth birthday the two had sex for the first time, and they both loved it. Andi was a gorgeous five foot seven inches dancer, who was slightly heavyset in her stomach, but had beautifully toned legs, and tremendous G cup breasts to match her perfect and tight ass. Jack on the other hand was an All State Sprinter and stood just over six feet tall, he was all lean muscle, and had a somewhat feminine look to him.

College had worked out perfectly for the two so far, both of their roommates went home on the weekends, and so they were able to stay in each other's room and sleep with each other all weekend, and the occasional weeknight as well. Both Andi and Jack were fairly insatiable when it came to sex, but had kept it fairly, but not exclusively vanilla when they fucked. Occasionally they would role-play, but not often, and nothing terribly kinky. During the spring semester of their freshman year that all changed.

The first Friday back from winter break Andi popped down to Jack's dorm room, which was one floor below hers. Jack let her into his dorm, and told her that he needed to take a quick shower and asked her to find a movie for them to see that night. As Jack exited the room, Andi pulled out his laptop and saw that Jack had left a browser open with movie times at one of the local theaters already up. She also saw that he had another browser running in the background.

Andi knew that Jack's showers after track practice took at least fifteen minutes. She had never snooped on his computer before, but was curious what he might be looking at with multiple browsers open, she had a guess that it was probably porn, but wanted to know more than just that. Andi looked at the clock and figured she could snoop for five minutes and then go back to looking at movie times.

Andi was not prepared for what she found when she switched browsers, she knew Jack liked porn, he had never hidden that from her, and on occasion they had watched scenes together while touching each other. What they watched together however had always been fairly mundane guy on girl or maybe two guys on one girl. Jack had open, and was clearly in the middle of watching, a fairly heavy Femdomme porn session. In the scene that Andi had interrupted during the woman was sitting on the man's face, with her high heels pinning the man's wrists.

Andi watched a minute or two of the scene and was incredibly turned on. She never realized that her boyfriend wanted something like this. She then clicked into his "favorite" list and found that the list was exclusively females dominating males, and two movies involving "mommy" punishing, or treating her son/step-son. Andi was literally soaking through her panties from the excitement of snooping, and seeing what her boyfriend wanted to have done to him. Andi quickly looked at the tags of the most watched videos and found that what Jack really liked was: Smothering, Forced Cross Dressing, Forced Bi, Forced Cumeating, Strapons, and Anal Fingering.

Andi looked at the clock and figured she had one more minute left to snoop. She looked at his bookmarks, and saw that three of them were to different sex toy stores. Andi figured out the handful of toys that Jack looked at most frequently, and made a note in her phone which ones she liked too. Then she reset the porn browser to the correct moment in the porn, and switched back to looking at movie times. Within two minutes she knew which movie and when they would go to, and decided to treat her boytoy when he got back.

Andi stripped and got on all fours in a position where Jack would see her immediately when he walked into the room, and in which she could send a picture of her ass taken in the mirror to him that just said "hurry up, I need your cock."

Within minutes of receiving the picture text Jack was back in his dorm room, and had let his towel drop to the floor. The whole time she waited for him Andi had been teasing her slit and working out an idea in her mind of how she was going to dominate her Jack the following weekend. Jack positioned himself behind Andi when he walked in and rubbed his cockhead against her insanely wet cunt. Andi loved the feeling and the anticipation that came with it. Jack had a great dick, it was a good six and a half inches long, with a great girth, and a tremendous mushroom headed cock.

After two or three minutes of teasing Andi thrust herself backward taking all of Jack's cock into her. "Fuck me rough baby." Andi grunted as the cock plunged into her.

For fifteen minutes Jack pounded in and out of Andi, and the sounds of their bodies slapping against each other reverberated around the small dorm room. Jack could tell he was getting close to cumming when he grunted "where do you want me to cum baby?"

"In...uh fuck oh fuck fuck...me" Andi moaned out as a second orgasm crashed into her.

Within another three minutes Jack came hard inside of his girlfriend's cunt. Andi pulled herself off of his cock and then spun around and sucked his softening shaft into her mouth licking it clean, it was mostly her cum and very little of his but she wanted to start breaking Jack into what she wanted him to be now, and wasn't fully satisfied with waiting a week, she stood up and drove her tongue into Jack's mouth. While they kissed Andi forced some of their joint cum into Jack's mouth and deep into his throat with her tongue.

Over the next week Andi took care of buying all the necessary toys she would need for the following weekend. The second weekend of the semester was a long weekend in honor of the Martin Luther King holiday, and Andi knew her roommate Sam would be gone the whole time.

Andi bought several toys, a nice strap on cock that advertised itself as for beginners, three different sized butt plugs, a lot of anal lube, and three pairs of panties. On Thursday night she went to get a manicured, and had her long nails painted a dark crimson, which she knew would drive Jack insane.

On Friday at 3pm Jack showed up at Andi's dorm, exactly when she had told him to be there. She let him in and immediately pushed him against the door and started kissing him. While they made out Andi stripped Jack down to nothing and slowly teased his cock with her fingers. She then sat down on the lower bunk of her and Sam's beds and spread her legs, Jack started to position himself to fuck her, and instead she leaned forward gave his balls a firm slap, and said "no, eat my cunt first."

Jack quickly dropped to his knees and started sucking on Andi's clit, he was more turned on than he had ever been before. Andi's tone, and the slap had caught him totally off guard, but he loved how domineering she was being. After she came once Andi forcefully pushed him onto his back and kneeled over him so that her cunt was inches off of his face.

Andi then positioned her legs so Jack couldn't move his arms, and she told him to take a deep breath. As he did Andi dropped her pussy onto his face and instinctively Jack began to eat her out. Every few minutes Andi lifted up enough for him to get a breath and then would drop back down forcefully. Andi wasn't fat, but she was big enough that the drops hurt, and shocked Jack every single time.

After twenty minutes and two more orgasms Andi moved around so that her face was pointed to Jack's cock. Jack was still pinned and couldn't move when Andi swirled a finger around the top of Jack's dick and gathered all of the pre-cum off of it.

She leaned backward, stuck her finger in Jack's mouth and said "lick it clean."

Jack hesitated and only complied after Andi again slapped him hard in the balls. After he ate his pre-cum Andi leaned back so her asshole was on Jack's mouth, and as she did so she hooked Jack's legs back so his ass was exposed in the air. Jack heard, and then felt Andi spit onto his ass before one of her fingers teased his asshole.

"So I have to admit, curiosity got the best of me the other day, and I was looking at what kind of porn you like." Andi said as her finger continued to circle Jack's asshole. "And I was very shocked and aroused to find that you like woman to be in control, and that you clearly wanted to be dominated roughly by a woman."

Jack moaned in agreement.

"So I decided I would make that happen for you." Andi said before again spitting onto Jack's ass. "So this weekend, and if it works for both of us for the foreseeable future, I'm your Mistress, and you will address me as such." Andi continued.

"Yes Mistress." Jack cooed out in a happy, but fearful tone.

"Do you want me to finger your asshole? Do you want to be my little assboy?" Andi asked in a sneering tone.

"Yes Mistress, oh please Mistress will you please stop teasing my ass and fuck it." Jack begged.

Andi gladly complied, by sliding one finger into her boyfriend's tight ass. Andi rapidly slid her finger in and out of Jack's ass, getting wetter and wetter as she heard his moans beneath her.

"Lick my ass" Andi told Jack "You can cum once I've cum from your tongue in my ass."

For fifteen minutes Andi and Jack went on like this until finally she couldn't resist the orgasm any more and bellowed at Jack "cum right now cum."

On command jack did as he was told and blew a load onto Andi's leg.

"Lick your cum off of my leg." Andi said as she moved herself off of Jack's chest, and positioned her thigh right in front of his mouth.

Jack was panting and trying to catch his breath when he timidly let his tongue graze Andi's thigh. In exchange Andi took all of the cum off of her leg with her fingers and shoved them into Jack's mouth shoving them deep in and forcing him to gag.

"Don't worry" Andi said as Jack choked around her fingers "you'll get good at eating cum eventually."

Andi then told Jack to get dressed but stopped him as he started to put on his underwear. "Oh wait!" Andi exclaimed "you don't get those this weekend. You get these." As the words left her mouth Andi produced a small pink thong.

"I want you in panties all the time, I know how much it clearly turns you on, it was a central theme in some of your most watched movies." Andi said with a grin. "Every time we go out this weekend you're going to be wearing a pair of slutty little panties that I bought for you."

"Yes Mistress." Jack replied looking down to hide how red his face was becoming.

As he slid the panties on his cock twitched at the touch of the soft fabric. Jack was embarrassed, and aroused at the sight of himself in the mirror.

"Awwww I like you in panties." Andi said with a little giggle. Andi knew that this was only the beginning of how far Jack was going to go in terms of cross-dressing, but for the time being she was opting to keep that fact to herself.

Jack finished getting dressed and the two went out to a movie and to dinner. During the entire movie Andi kept teasing his balls through the thong's fabric. She had unzipped his fly, but let his cock remain inside of his pants, and instead just gently grazed it every once and a while during the movie. The sensations were almost too much for Jack and at multiple times he almost came inside of the panties.

After dinner and the movie Andi and Jack went back to Andi's dorm room. Once inside Andi told Jack to strip down to just his panties. Jack rapidly complied, hoping that a release would be coming soon. Instead Andi sat down on the futon in her room and made Jack give her a long foot massage. Once the foot massage was done Andi spent fifteen minutes giving Jack a long strip tease, and then once naked ordered Jack to give her a full body massage.

While in the middle of the massage Jack squeezed Andi's ass in what she deemed a "sexual not relaxing way." Jack had no idea what exactly that meant, but understood the anger that she was showing.

"You get to touch me to turn yourself on only when I say you can." Andi said as she walked to her closet.

Inside of her closet Andi pulled out a Rubbermaid tub. Inside Jack could see all kinds of clothing, and what he distinctly recognized as a flogger with dildo on the end of it. Jack had been drooling over the device for months.

"Panties off." Andi barked.

Jack rapidly complied, and as he did so Andi marched over to him and grabbed his balls hard in one hand and pulled Jack to the foot of the dorm's bunk bed. Jack stood upright, and as he did Andi took rope and tied Jack to the bed with his arms spread above his head and tied to both bed posts, and his legs tied spread to the bottom of the bed.

Without warning Andi hit Jack hard with the flogger. The leather burned as it lashed across Jack's upper back. His girlfriend then systematically worked her way down slapping the hard flogger down each inch of his back, his ass, and finally his legs. While Andi was hitting him Jack fought the urge to cum, when the blow beat across his ass it was nearly impossible and Jack found himself bellowing a thank you out with each hit.

Once Andi was done she walked behind Jack and rubbed his cock for a few moments. "Don't cum." She said as she did so. "Keep your eyes facing forward, you took that punishment really well, better than I thought you would, and now you get a reward."

When Andi next approached Jack he felt her fingers coated in anal lube rub around, and then inside of him. Andi slowly fingered Jack before inserting the back end of the flogger into him. Jack moaned, and almost came immediately as the flogger handle penetrated his virginal ass.

"Oh my god Mistress, can I cum please? It feels so good but I can't resist please Mistress let me cum." Jack begged.

"Not yet." Andi replied.

For ten minutes Andi fucked her boyfriend slowly and gently with the dildo on the back end of the flogger. Abruptly she stopped and rapidly withdrew the toy from Jack's asshole.

"Oh no Mistress please, please don't stop I'll do anything just don't stop." Jack cried out as tears filled his eyes from the denial of the orgasm.

"Shhhh it's okay" Andi said as she rubbed the exterior of Jack's ass with her fingers. "I'm going to put a plug in you for now, and when I cum a few more times then you can cum."

Andi slid a butt plug that was medium sized into Jack's ass and untied him. She then sat on the futon and told him to crawl over to her. As he did so Andi produced a different dildo and a vibrator for herself.

"Suck on my toes." Andi said holding one foot in front of Jack's face.

Jack quickly complied and as he did so Andi turned the vibrator on and slid the dildo into her pussy.

"Don't worry baby, your tongue is going to get its turn soon." Andi said mockingly. "And if you're really good your dick will to."

Andi was being honest about Jack being able to fuck her, as much fun as toys and his tongue were from time to time Andi knew she would need a cock to make her cum. Andi began fucking herself more rapidly as she barked at Jack to switch feet. The orgasm kept building until finally Andi tossed the vibrator and dildo aside and furiously rubbed her clit with one hand while sticking three fingers inside of herself with the other. Again Jack felt the impulse to cum without any touch at all.

As the orgasm rippled through Andi and she let out a loud scream she reached down and pulled Jack into her cunt before shaking her head, pushing him back harder than before and straddling his face.

"Eat my out my little bitch, make me fucking cum again." Andi growled through clenched teeth as she fought back a scream.

Andi came within only minutes the first time, but the second time fought off an orgasm for nearly a half hour. When she finally did cum Andi told Jack he would get a good reward for his patience, and perseverance.

Andi began to suck Jack's cock, and every time she felt him get close would stop and tell him to suck her big toe for three minutes. For almost an hour Andi painfully edged her boyfriend, slowly adding different motions than just a simple cock sucking, she began to play with his balls, and then to move the butt plug in and out of him.

After an hour Andi stopped the teasing and said "if you can last five whole minutes without cumming then I'll let you cum in my mouth, if you can't then I won't let you cum at all tomorrow."

Andi promptly set a timer on Jack's phone and proceeded to give Jack the mother of all blowjobs. For five minutes Andi bobbed up and down on his cock and then alternated between bobs and tongue swirls, all the while Andi was slowly fucking Jack's ass with the butt plug. At five minutes the timer went off and Jack almost immediately exploded a huge load into Andi's mouth. Ordinarily Andi would have swallowed it all. Instead she began to kiss Jack forcing more than half of the load into his mouth. Jack fought back at first, but eventually relented and swallowed every ounce of cum she gave him.

Andi and Jack then got ready for bed. Andi told Jack to put on his thong again which he sheepishly did. Then as he went to his bag to grab a pair of shorts to sleep in Andi again stopped him.

"Silly little boy, this weekend you're dressing like a girl when we are in here!" Andi exclaimed in her giddiest voice possible.

She then went into her closet and pulled out a silk babydoll to match his thong. Jack stared dumfounded at Andi for a few moments before putting it on. He was mortified when he looked in the mirror to see how feminine he looked dressed in the slutty women's clothes Andi had put him in.

The two laid in Andi's bed, and eventually fell asleep. While she drifted off to sleep Andi contemplated what she had in store for Jack on Saturday.