Descent into Debauchery Pt. 10

(Thanks to Drewau for editing. Comments and feedback always welcome and appreciated. As with most of my stories, it is advised to read the previous chapters for context.)

"I know how we can get Jenny." Mary Ann said as she laid naked on Nicci's bed. All three were nude actually. Tom was sandwiched between Mary Ann with Nicci in front of him. They were all sweaty and breathless from the hour long threesome they had just taken part in.

Nicci was nearly asleep when she heard the statement. "What was that?"

"Jenny, I think I finally have a plan to get her into bed." Jenny was a cute 18 year old who lived across the breezeway from Mary Ann. Tom and Nicci had come to notice her the night that they first met Mary Ann in the laundry room. Her tight body, scant clothes, and ultra sexy dance moves had charmed them all.

"What's your plan this time?" Nicci asked. They had already tried a couple attempts since that adventuresome night.

The first try had been simple, Tom tried flirting with her. But, as Tom had little experience with that, the plan failed miserably. The second attempt had them trying to tempt her at the pool. Nicci and Mary Ann wore such revealing bikinis they worried they might be arrested.

Mary Ann wore a micro bikini that just barely covered up the bits that were required by law. And then that was only when she severely limited her movements. Nicci wore a one-piece that was quite sheer, especially once it got wet. They considered putting Tom in a speedo, but thought that might be a bit too much. Tom wasn't comfortable with the idea either.

Nicci teased him that he could screw her outside in front of a crowd, but he was too shy to wear a speedo at the apartment pool. He explained that he would go nude if he didn't think he would be arrested immediately. But a speedo would be uncomfortably tight, especially since he would have an erection from seeing the two of them in their suits.

That actually gave them the idea for what he should wear. Loose swim trunks with the net inner lining cut out. That would make his erection glaringly obvious, but still give him plausible deniability.

When they got to the pool, they saw Jenny dancing to some music on her phone. She was wearing white bikini bottoms with ruffles on them. Her top was small light blue triangles that barely kept her decent. Tom already had an erection before he arrived at the pool. Seeing Jenny wiggling her cute butt around really made him tent.

The three arrived separately, as they thought traveling in a pack might intimidate her. The also each had a plan for how to seduce the hot coed. Mary Ann went first. She asked her to rub some suntan lotion on her back. Jenny complied, even rubbing it into her glistening cheeks. Mary Ann turned over and asked her to help her with the front now.

Jenny was no idiot though and told Mary Ann to get herself off, because she wasn't going to do it. Jenny reminded Mary Ann that she wasn't into girls. Mary Ann took her advice and began fingering herself right in front of the girl. Jenny got flustered and moved to the other side of the pool deck. Mary Ann finished herself off while watching Jenny walk away.

Nicci was next up to bat. She wasn't quite as bold as Mary Ann. She strutted in and dove into the pool. Nicci swam across and exited right in front of Jenny. Her swimsuit was now completely transparent. Jenny took notice immediately and warned her that she was exposed.

Nicci released her most ditzy airheaded laugh possible and said. "I guess you're right. Well, it's just us girls here, I think I'll just take this off." And then she peeled the one-piece off right in front of her.

Jenny rolled her eyes and moved again. This time to a small alcove somewhat hidden away from the rest of the pool area. This was where the hot tub was. She climbed into the hot tub, spread her arms wide along the edge, and reclined her head back. This made her hotter in two different ways. One, her exposed neck was begging to be kissed, and the bubbles were making her breasts jiggle beautifully.

When Tom entered the picture he couldn't think straight. The sight of her made his erection drip a little precum. Tom hadn't been able to think of a plan beforehand, and now his mind was completely empty. So he sat on one of the lounge chairs and just watched her beautiful softballs bounce in the waves from behind his sunglasses.

After about 5 minutes, Jenny climbed out of the pool and noticed his massive erection immediately. Instead of stomping off offended though, Tom swore he saw a slight smirk raise the corners of her lips briefly.

Jenny grabbed her sunscreen and began slathering it over her legs. Tom watched as her hands glided up and down her smooth tanned legs. Then she began smearing the creamy liquid across her smooth stomach. Tom nearly came when she dripped the white lotion onto her chest.

Tom had to close his eyes and breath deeply to calm himself. A few seconds into this routine, he heard Jenny call to him. "Excuse me. Do you mind doing my back?"

Tom opened his eyes to see her extending the bottle out to him. "Umm... Yeah... Sure." Tom stood and her eyes immediately fell to his tent again. She said nothing but turned and laid on her stomach after handing him the bottle.

Tom drew a line down the back of her calves and hamstrings, set the bottle down, and rubbed it in. When he got to her hamstrings his hands got closer and closer to her crotch with every up sweep of his hands. On his final movement, his middle finger just barely grazed her pussy through her bottoms. This made Jenny shiver. When he repeated the same actions on the other leg, a little moan escaped her lips.

Jenny reached behind her and undid the strings of her bikini. "I hate tan lines."

Tom was actually in pain now from how much his shorts were restricting his boner. He couldn't take it anymore. She was looking down through the rubber slats of the lay out chair. He figured she would never see what he was about to do. He just had to have some relief from the pressure. So, he pulled his shorts off as quietly as possible.

Tom would have sworn the act of freeing his member made it grow another half inch. But he had to focus and continue spreading the lotion or she might turn around to look. So, he drew a couple lines on her back and began rubbing it in. Touching her warm supple flesh was driving him wild. He felt like he could go at any second.

"I really hate tan lines. Would it offend you if I pulled my bottoms loose and you creamed my butt as well? I mean, it is just a butt, everyone has one."

Tom barely squeaked out a response. "No problem."

"Thanks." Then Jenny pulled the strings of her bikini loose and lowered the back down exposing her gorgeous rear end to him. Tom had the brief observation that she was telling the truth about hating tanlines, before he came on her cheeks.

His cumshot had four bursts. One, stretched from her lower back down her right cheek. Two, traced down her left cheek. Three, crossed both cheeks and made a little bridge across her crack. Four, drew almost a perfect line down her great divide.

Tom was horrified. What had he just done. But, she didn't respond, so she must have thought it was lotion. He quickly dropped a few more drops of lotion on her cheeks and began rubbing it in.

"Yea, put some extra lotion on there. Nothing worse than a burned butt. You have to lay on your stomach for a week."

Tom began rubbing the mix of fluids into her butt. "You've experienced that before?"

"Oh yeah, I went to a nude beach with some friends of mine for spring break. I fell asleep and burned my entire back side. My butt got the worst of it though. At the time it had never seen the light of day, so it was as pale as the moon."

Tom laughed at her pun and kept rubbing. "Make sure you get it well in the crack too. Burned cheeks rubbing together is about as bad as it can get."

Tom spread her cheeks and even grazed her hole with his fingers. That made Jenny gasp, but not object. So, Tom did it again. She moaned this time. The third time Tom let his fingers move all the way down and graze against her pussy. Jenny moaned loudly.

Suddenly, a ringtone pierced the air. He recognized it to. It was a video call, and it was coming in to Jenny's phone. She picked it up and Tom could see the caller id, "Mom." He then had instant clarity of his situation. He was butt naked sporting a new erection, and Jenny's mom was about to see everything.

Tom grabbed his shorts and sprinted back to the pool area. Nicci was still laying out naked. As he was approaching her, they heard several voices coming around the corner. They were both about to be found out. Tom grabbed her hand and they slid into the Ladies changing room.

Nicci noticed his state of undress and asked how far he got. He told her the whole story, and at the end Nicci said, "You know, I could use some sunscreen." Without another word, they began kissing and were both cumming in minutes.

The third attempt fell into their laps when Mary Ann was checking her mail. She noticed a flyer on a bulletin board asking for a math tutor. And who was the tutoring session for? None other than Jenny Buchanan herself.

"I think you've watched too much porn." Tom teased. "Not every student wants their teacher."

Mary Ann rolled her eyes. "I know that, but look at the details. The lessons have to be at her apartment, and they have to take place at 10:00 at night." Nicci and Tom stared at her blankly. "People are most comfortable in their home. Not to mention how late it will be, maybe she will get a little loopy from sleep deprivation. Then there's the fact that our lessons will be free. College students love free stuff."

Tom and Nicci couldn't argue with that. Whenever they went out to eat Mexican, they would always fill up on chips so that they could make two meals out of one. They also took as many free samples as possible at the grocery store.

"So, who gets to be the lucky tutor?" Tom asked.

"Well, it can't be me." Said Mary Ann. "I think she would instantly suspicious of my motives." She looked at Tom, "How good are you at math?"

Nicci let out a burst of a laugh. "That bad huh?" Mary Ann continued.

"Let me put it this way." Nicci explained. "I've had to start offering him a blow job every time he does his homework. To keep him motivated."

"Then what about you?"

"I could do it." Nicci agreed. "I mean, I think Tom would have a better chance after what we saw at the pool. But there is no way he would pass as a math tutor."

So it was decided, and Nicci called and set up the tutoring session. Mary Ann helped Nicci pick out the most subtly seductive outfit they could find. She wore no underwear, yoga pants that were so tight that they rode up both slits, and a sports bra. The story they were going for was that Nicci had just finished working out and came straight over.

Tom couldn't keep his hands off of her. He tried to convince her to have a quickie before the session but they didn't have time. Mary Ann ended up having to distract him so that Nicci could leave. "Tom, how about a wrestling match?" Tom looked at her confused. "Have you ever heard of Ultimate Surrender? Basically, we attempt to wrestle each other out of their clothes, and try to make them cum. The first to cum loses.

That got Tom's focus, and he quickly forgot about Nicci as he was already pinning Mary Ann to the floor. Nicci almost wished she could stay and join in the festivities. But she had her own opponent to conquer.

Moments later she was knocking on Jenny's door. To her surprise, she was not the one to answer. A woman in her late thirties did. She actually looked very similar to Jenny. She was older, taller, and had wider hips, but that was not a bad thing.

"Is Jenny here?"

The woman stuck out her hand. "That's me."

Nicci shook her hand but had an apparent look of confusion on her face. The woman understood immediately. "You thought you were tutoring my daughter."

"You're both named Jenny?"

"Yep. I know it might be vain of me, but I figured if men could name their sons after them, why couldn't women? To be fair I stole the idea from the Gilmore Girls."

"Oh, I love Gilmore Girls."

"Me too. If you could only see the fantasies I've had about those two."

The statement shocked Nicci into silence.

"I'm sorry. Did I share too much? Jenny is always getting on to me for that."

"No, it's fine. So, you're a lesbian?" Nicci knew the question was awkward and inappropriate, but she was struggling to keep conversation going as she attempted to come to grips with the onrush of new information. Her plans had flown right out the window.

"Not exclusively. To be completely honest, I'll screw anything that can give me a great orgasm. If I met an alien tomorrow, I'd be asking it if it wanted to do some anal probing. And you should see my toy collection. Oh, have you ever tried a sybian? I just got one, and I'm not sure if I'll need a warm body ever again. I'll let you try it out if you want. But only if I get to watch."

The woman's rapid fire speech was enough to make Nicci's head spin. Let alone the actual words she was saying. "Umm, maybe later. Where do you want to do this?"

"Oh, I'm easy. On the floor, in the bed, the shower's fun. Dangerous but fun." It took Nicci a second to realize she was kidding, or was she. Jenny laughed and led her to the couch.

"So, you're in school?"

"Yep, started night classes as soon as Nicci graduated."

"Is that why I've never seen you around?"

"Sadly yes. I work two jobs and go to school at night. That was why I needed to do this so late. Thanks for being so accommodating by the way."

Nicci helped Jen, as she quickly explained she liked to go by, with her homework over the next half hour. Jen finally called for a break as her brain felt like it was about to fry. "I haven't had to think about this stuff in nearly 20 years. And even then I wasn't any good at it. Do you want a drink?"

"Yeah, just whatever you have on hand would be fine. Thanks."

"So, how do you understand all of this so well." Jen called from the kitchen as she was shuffling around and preparing their drinks."

"I look at it as a real world puzzle. For example, I want ice cream for dessert, but I don't want to gain weight. I know how many calories are in the ice cream, and I know how many calories, roughly, I burn running. So I just have to figure out how long I have to run to burn said number of calories. That is the X, or the variable."

Jen walked back into the room and handed Nicci a glass with a purple liquid inside. Then she sat down beside her with her own glass. "OK, I think I get it now. Here's one. The outcome is that I want to have a threesome. I'm a definite, and so is my partner, but the third party is the variable."

Nicci almost spit her drink out, but not because of what Jen had said. In the last thirty minutes nearly every other comment out of her mouth had been some form of dirty joke or tease. She had gotten used to that. What she hadn't expected was the wine.

Nicci was 19 and had never drank alcohol before. Part of her strict upbringing. She thought about telling Jen that she couldn't drink it, because she wasn't 21 yet, but then she held her tongue. What's one more forbidden fruit? And she really liked grapes.

Sadly the taste didn't transfer. She had to choke the wine down as she hated the taste. But she was determined to find out what being buzzed felt like. After about 15 minutes and three quarters of the glass was gone, Nicci was pretty sure the alcohol was starting to take effect. She felt warm all over and a little giggly.

She also noticed she was getting a little more touchy feely. Nothing scandalous, a hand on a knee as she bent over laughing at one of Jen's dirty jokes. But that was a lot for Nicci, she had been very guarded with any kind of physical touch. Even a friendly hug drew dagger eyes from her dad growing up.

"That's it!" Jen declared. "I can't take this anymore. The bra is coming off. This thing has been digging into me all day."

Nicci sat and stared in amazement as Jen reached under her t shirt and undid her bra. She pulled her arms inside her shirt and slipped the bra off without exposing an ounce of flesh. Despite that fact, Nicci suddenly felt intensely aroused.

She eyed this older woman as she took another drink of her wine. Nicci came here for Jenny, but her mom wouldn't be a bad silver medal. The more she thought about it, she thought that Jen might be the better prize anyways. Jenny would probably be too timid and inexperienced. Jen, on the other hand, sounded quite experienced.

"So, back to the earlier topic." Nicci said as she gently grazed her foot up and down Jens shin. "Who would be the variable in your threesome?"

The statement nearly made Jen spit out her wine this time. She sat the glass down on the coffee table and said, "I'm sorry. My teasing went too far. This conversation is really going where it shouldn't."

Nicci gave her best confused innocent expression as she said, "What do you mean?"

That look drove Jen wild. She had had too many school girl fantasies. Some where she was the innocent school girl, and some where she was the teacher. "Look, you are a beautiful young woman, but I wouldn't feel right having a threesome with you. You're probably about the same age as my daughter."

Nicci played dumb and said, "Oh no, I was just asking hypothetically. Like what celebrity."

Jen stared at her for a second and relaxed a little. Then she laughed in embarrassment. "I'm sorry. I thought you were coming onto me." Then she picked up her wine glass and took a sip as she thought hard about the question. "Well, I'd take any of Anna Bell Peaks, Brandi Love, or Diamond Jackson. Although, Corey Chase would come in a close fourth."

Nicci looked at her confused. "I've never heard of any of them."

Jen smiled big and chuckled as she said, "We have to rectify that now." She sat her glass down again and pulled out her phone. Nicci set her glass down as well and cuddled up close so that they could both see the phone at the same time. "They are four of my favorite porn stars."

Nicci felt butterflies in her stomach. Was she about to see porn? Despite everything she had done so far, this was a simple line she had never crossed. She crossed her legs as she felt herself getting moist. Jen flipped through countless images and videos on her phone.

As hot as it was seeing porn for the first time, and with another incredibly hot woman beside her. What Nicci noticed most was the slight wet stain between Jens legs. It was barely visible, but it was there. Jen was also squirming slightly and clenching her legs tight.

"They are incredibly hot. "Whose breasts do you think are bigger? Mine or Corey's?"

That question made Jen uncomfortable again. "Umm, I... I don't know. I mean I haven't really seen yours." Jen hadn't been hinting at anything, but Nicci jumped on the chance and stripped her shirt off.

Jen just stared at Nicci's large breasts in shock and awe. Her mouth was hanging wide open. "I, I, I... I think you should put your top back on."

Nicci acted hurt. "Why? Are my breasts ugly?"

"No, they are quite... beautiful. But like I said, you're nearly the same age as my daughter."

"And?"

"And, that would feel wrong."

"But you haven't even felt them yet. Here." Nicci grabbed Jen's hands and pressed them into her soft warm flesh.

As much as Jen felt like she needed to remove her hands, she just couldn't. She was enjoying them too much. "We shouldn't be doing this." Jen said as her gaze never wavered from Nicci's tits.

"How are they in comparison to yours?"

Jen laughed and said, "Now that... that is taking this a little too far." She removed her hands and Nicci took the moment to quickly grab Jen's shirt and lift it off and over her head. Jen's eyes went as wide as her large areolas.