The Deepest Friend-Zone Ch. 06

Connor nervously paused knowing he would say yes while images of a naked Sarah once again flooded his brain. "Yea, definitely. I could use any help I can get at this point."

"Great! Are your roommates there at this point?"

"They shouldn't be. Kevin is usually in class by now, and Lee is always at the gym by this time."

"Let's go there then. That will be more quiet than having to deal with the girls."

"You don't want to go to the library?" Connor said hesitantly, immediately realizing how this was a stupid ask.

"Nah, too many people. Let's just go to your place."

Connor caught on that Sarah had an idea of what she wanted to do since there was usually no on at the library at 9am on a Monday. Who was he to protest some alone time with his crush? This automatically brought butterflies to his stomach being his first true alone time with Sarah that was not in public.

Of course his mind further raced as they began to walk out of the classroom. First, thinking back to who he thought was an innocent and sweet freshman girl, with her hair pulled back by a jacked jock in a basement grind pit. Then to watching this same sweet girl moan and orgasm on top of a huge cock that she took with ease. His nerves grew knowing that he could not perform like Joe did this weekend if this wound up being his first fuck ever.

"You're quiet today? You usually can't stop gossiping with me!" Sarah accused Connor, but in a teasing tone with a smile. Connor was caught off guard and quickly tried to think of an answer that did not involve thoughts of a huge cock up Sarah's cunt.

"I'm quiet? I didn't realize. Sorry. Maybe I'm just tired on a Monday."

"Gotcha. I just hope it is not because of Saturday night. I wouldn't want something like that to ruin our friendship. Weird stuff happens all the time at our place. You get used to it faster than you would think. "

There it goes. She said it. Cat's out of the bag. Connor knew it was going to come up but wasn't expecting it on a walk through campus. There really wasn't a time that was convenient. How do you even respond to that? Connor had an internal debate about whether he was more turned on or upset that he watched his crush get fucked. And to see how Sarah and her friends were so cool about the whole situation was even more thought provoking. How often do they do things like that? He had to say something quickly. It was more awkward to stay quiet.

"That was a common occurrence?" Connor cringed, knowing that this line of questioning would more than likely lead to answers he did not want to hear. Not knowing was bothering him equally as much.

Sarah had to make a choice at this point. Change the topic and divert, keeping things in an awkward don't ask, don't tell position; or, she could let him in fully. Fully put him in the friend zone and telling him about her sex life, possibly ruining their friendship and creating an awkward dynamic if he reacted poorly. There was no getting away from each other being in the same academic program. This would go well, or horribly with little room for anything in between.

"Well, yea! When you get horny all the rules get thrown out! We have all gotten pretty comfortable and open around each other. We even play around with each other and share guys. It's all in great fun!"

Connor's heart sunk hearing Sarah was nowhere close to the innocent girl he thought her to be. Sarah was almost some type of deviant. They share? How many men could she have possibly fucked already? He always had a thing for cuteness and innocence. She also further confirmed his status as only a friend. The thoughts circling his head were rather confusing. One one hand, it was amazing that this beautiful and kind woman wanted to be around him and trusted him enough to tell her about her private life. On the other, it was painful to hear that she was this sexually open but not available to him. Connor's horniness was building faster than his disappointment and compelled him to learn more. He was not even sure if it was actually the shame that was turning him on.

"Wow. I mean, I thought things like that only happened in porn or were made up by guys that wanted to puff their chest out. Do you like, get with these guys again? Or was that just a one time thing?"

"Well, I bet there are a lot of guys who lie about that kind of thing, but they probably are not the ones ever getting laid. I tend to keep guys around as long as they do a good job. I mean, I'm not looking for my husband so if they suck in bed, we are done quickly. I probably have about seven or eight guys I hook up with now and again. Some more often than others. There haven't been too many that were one night stands."

Connors head spun further as they approached his dorm and he pulled his key card out.

"Seven or eight? How often are you getting laid?"

"Uh, daily? How long can you go without getting laid?"

Connor reflexively froze and looked at Sarah while walking up the stairs. Sarah's eyes grew a bit knowing exactly why he froze.

"Well, definitely not that often." He awkwardly tried to laugh off the lie.

"Wait, Connor. Really? You're a virgin?"

He had been caught. His experienced, slut of a crush was in his dorm building, and figured out that not only is he not sexually experienced, he hasn't had ANY experiences. Knowing that she doesn't even give underperformers a second chance makes the whole conversation more embarrassing. Connor's brain quickly highlighted Joe's skillful pleasuring of Sarah, quickly playing back the orgasms he elicited from her.

The door one flight of stairs up from them opened and caused an immediate feeling of relief for Connor, knowing that their conversation would have to wait until they were once again in private. A cute blonde girl came quickly down the stairs, appearing to be in a rush. She looked at the two in passing but had no greeting or expression.

Connor and Nina continued up to the 3rd floor and suspended their conversation until Connor was able to open the door and get them inside the triple dorm room. His heart once again began to race and the bit in his stomach grew being truly alone with Sarah for the first time.

"Not once Connor?" Sarah pushes for answers.

"No! It sucks! I wind up being friends with all the girls I like. I don't get how it works. And here I am, again. I really like you, Sarah. You're so pretty and fun to talk with, but obviously you want nothing to do with me romantically. I mean you're schedule already seems to be full with guys keeping you satisfied and I can't even find a girl that wants to fuck me!" Connor snapped.

All of his feelings came out at once and as soon as he started, the emotions were not going to stop flowing. Sarah was definitely not expecting all of this to come out now but she was far from surprised. Connor was always way more polite and nice to her than a normal guy her age, showing his hand at how he viewed her but was definitely not attracted to him in a sexual light. There was a minor portrayal of hostility and jealousy with Connor's mention of her promiscuity, which partly pissed her off but also made her feel hot and in control. She had to formally engage the friend zone which was never a pleasant experience, but she was intrigued to see Connor react.

"There are plenty of girls that would be happy to fuck you, trust me." Sarah started on a positive note. "We are definitely awesome friends and I can tell that we will be even better friends over time, but I don't think that will come with any sexual feelings. If it bothers you, I will never talk about any of my hook-ups again. It was probably fucked up to even let you stay while we fucked around this weekend."

Connor was not entirely crushed by Sarah's words because he had assumed her feelings were as such, but it was not pleasant to hear in the least. His horniness had taken over at this point and wanted to ensure that if he couldn't have Sarah for himself, at least he could hear about her conquests to keep in his spank bank. Maybe she and her roommates would even let him watch again. The ice had already been broken.

"No! It wasn't! It was a surprise at first but it definitely wasn't an issue in my eyes. And you can talk about whatever you want. Isn't that what great friends do?" Connor said hastily to make sure Sarah spent no time feeling awkward.

"I guess it is." Sarah smirked. "You even like it a little bit. Don't you?"

"It's hard to say that it doesn't get me interested." Connor sat down at his desk as the pace of the conversation settled.

"Seeing you watching Nina this weekend was sexy as hell. It was obvious how much it turned you on. The both of us were definitely more horny because there was an onlooker."

"She is one horny woman, isn't she?"

"You don't even know the half of it Connor." Sarah said defiantly as she stepped toward Connor. "This lotion and tissues on your desk wouldn't happen to be for when you jack off, would it?" Sarah continued toward Connor to stand over him. His eyes instantly widened as his head whipped towards his desk to look at the embarrassing setup.

Connor never even thought about the arrangement on his desk. It was just conveniently set up and he did happen to jerk off there most of the time. Sarah was his first female visitor in the room so he never considered what might look incriminating. Connor mentally scrambled for an excuse, but his initial response had given him away. The conversation had already gone in an incredibly personal direction so he might as well continue.

Connor looked back to Sarah, who was now at a very intimate distance from him, making him a bit more nervous. Her cleavage was now at his face height and only about one foot away. Her breasts sucked him in, but he managed to raise his eyes to look her in the face again, now blushing.

"You caught me. Is it that obvious?" He pleaded.

"Well I assume you don't care much about dry skin, so yea. It's obviously your jack off station."

"Damn"

"Would hearing about Nina get you turned on?"

"Honestly, I've been constantly horny since Saturday night. This hasn't helped my cause. "

"Maybe as part of our friendship, I can give you a bit of relief, and tell you more about what the girls and I have been up to?"

Connor was completely taken off guard. Only a few minutes earlier, Sarah had told him that she did not have any sexual interest in him, and now she was hinting at getting him off. He pleaded inside that this meant she wanted to fuck him. Trying to make that happen would be a god send.

"Yea I'd love to fuck you. Of course!"

Sarah immediately laughed as she took another step forward to now stand with Connor's leg between hers while he sat sideways on his chair. She put her hand on the side of his neck just below his ear to cup his face.

"No. No. Silly boy. We will not fuck. Do not get that twisted. But I have no problem jerking you off. That is all I want to do to you. I wanna see how all that built up tension comes out."

Connor was royally confused. After being blatantly friend-zoned, he now had his crush holding his face and telling him that he cannot have her, but that she wants to give him a hand job. Part of him was hurt even further, but he was in no place to turn down his first sexual encounter.

"You, you do? I mean, yes I want that! Definitely! But like that's all you want? I'm confused."

"If I were you, I would take the offer. It turns me on to see you get hot and bothered. Someone also needs to take care of you because that is obviously not happening. But Connor, do not fuck this up. If you tell anyone that we are anything but friends and that we have this arrangement, I will make sure to publicly embarrass you. Is that understood?"

Connor was now as rock hard as he has ever been and his tip was pressing against Sarah's leg just below her skirt line. His mind was confused and worried about the prospect of being a public embarrassment, but his cock begged to have Sarah relieve him.

"Ok, deal."

"Great!" Sarah backed away. "Time for our first study break! Take those sweats off, it's story time." Sarah pulled his roomates desk chair over to sit in front of Connor as he hesitantly stood up and pulled his sweatpants down.

A million thoughts danced through his head. He had never shown his dick to any girl before and really didn't spend much time naked in front of anyone. Especially after watching the guys fuck Sarah and Nina this weekend, he knew his dick was relatively small and not a tool to show off or be proud of. What would Sarah think? Would she laugh? Would she insult him? She had been so nice to this point but getting her in an intimate setting seems to unleash a different side of her.

Sarah sat with her booted legs crossed and hands on her lap, assessing his dick with little expression. He stood in front of her half blushing and half horny as he had ever been. Sarah reached out under his balls with an open palm facing up and gently ran the underside of her fingertips and French manicured nails from the base of his balls to the tip of his cock. Connor squirmed as her index finger nail lightly grazed the underside of his cock head, causing him to pull away from the intense sensation.

"Take that shirt off and make yourself comfortable, this is going to be good time my friend." Sarah assured him in a calming tone but with a steady smirk conveying her control of the situation.

Connor did as he was told and took his Nike dri-fit tee off. He was not a huge fan of going shirtless due to his far from a chiseled physique. Connor stood at 5'8" 170 pounds. He was not fat, but soft was a good descriptor. Kind of a scrawny chub that only an Irish boy who had not hit full fledged maturity could muster. He had short, light brown hair that was a bit unkempt, especially when he attended a Monday morning class. He cut his hair every month, but was currently due for a trim, leaving him a bit more messy than usual. He had light stubble on his face, that was patchy at best, highlighting the fact that he was still maturing as a freshman in college.

Sarah continued to scan him from head to toe as he undressed and took a seat at his desk chair. Removal of his shirt revealed a slender but soft body with slight man boobs and an undefined stomach. His arms were not skinny but were definitely not the toned and muscular arms that Sarah craved in a man.

Connor's cock stood at full attention and was red with excitement. He packed 4 to 5 inches in length which was far from what Sarah looked for in a guy, although she had a few encounters with smaller cocks that she ended almost before they began. Connors cock size was not aided at all by his lack of grooming. His pubes had definitely been trimmed at some point, but not within the past month or so. His balls were shriveled up dude to being out in the cold earlier and seeking refuge in his body. Connors legs were equally as pale and undefined as his torso. As he finally sat down, he had a bit of a chub roll on his lower belly with a small happy trail running into the crease where his belly button hid.

"Sit forward and spread your legs a bit. Do you want to hear about my sunday with Nina? Or another time Nina has been a little slut?" Sarah began to speak in a sultry voice while rubbing Connors inner thigh. "Or maybe even about Jackie and the other girls? Or how about what I am planning to do with Joe and Paul this week?"

Sarah really knew how to mess with Connor's head, intentionally or unintentionally. Each one of her offers revealed more about her sluttiness and made him partially more curious, partially more jealous, and fully more horny. Sunday with Nina? Does that mean they got with each other all day? What do these girls do? He could easily imagine that there were stories enough to fill a book about Nina, and Sarah could tell him those any time. Jackie interested him very much, especially after he could hear her with the giant basketball player through her walls. He had no knowledge of the other roommates and would like to have a picture of them in his head rather than try to make it up.

Hearing that Sarah had plans with Joe and Paul took him back a bit. Was she planning to see them so soon again? The way she phrased it, she did not include Nina. So, did that mean she meant to have them both to herself? Did that mean that she had fucked Paul after Connor left as well? The thought of what she would be up to interested him the most, especially with his jealousy. Part of him hopes the plans might even change without knowing what they were at this point.

Connor was quickly jolted with pleasure yet again as Sarah very lightly grabbed his dick and slid from the head down to his balls with a feather touch, snapping him out of his debate

"What are you going to do with Joe and Paul?" Connor asked as he turned his head to look Sarah in the eyes. She gently threw her head back to adjust her hair with a smile as she grabbed the base of his cock to start jerking it while she spoke.

"Ughh, I just had a great time with them on Saturday night. I mean, its not that often that you find two friends who both know how to fuck like that. And on top of it they both had great cocks. Not as common of a combination as you would think." Sarah moaned slightly in recall.

"You wound up fucking Paul too?"

"Oh! he was great. Nina and I usually would have switched back and forth a bit more, but Paul and I got lost in each other for a long while. I swear, it was four in the morning before we even knew it. He just stays rock hard after he cums. It's incredible. His cock is just so thick and meaty too, it drove me nuts"

"So you want to fuck them again?

"I actually want to have a threesome with both of them to myself."

"A threesome?"

"Yes, Connor. I want both of them inside me." Sarah demeaned him.

"Do you do that often?"

"I actually had my first on Sunday! Well, kind of. Nina fucked my ass with a strapon, while one of her boy toys took care of my pussy. They actually took my anal virginity as well!"

Sarah could feel Conor's orgasm building a bit by the spasms in his cock and shifted her attention to his balls to slow the process down a bit. She loved how talking about getting fucked in the ass was getting him excited.

"She took your anal virginity with a strapon?"

"No way!" Sarah laughed as she went back to stroking his cock."Her friend Pete took it. Nina's strapon is like, eight inches or something and would kill me if I tried it first. Pete is only like 6 inches and not quite as thick, as well as being a phenomenal lover. I mean, Nina was able to get it into me after a bit of a warmup but no way was that happening first."

Visions of a tiny, tan, voluptuous Nina, fucking Sarah doggy style danced through Connors head. He could picture her slutty expression as Sarah would cum on her strapon while she pounded away. He wanted to hear more to further the image. Looking at Sarah in person was enough to get him to the edge but this visual was truly exciting him.

"What was it like having your first threesome?"

"Oh, so awesome. Nina got me horny as fuck in ther morning when we showered together, so by the time Pete actually got there, I was ready to jump him. He was so good at controlling me. It was like he knew exactly how to get me to the edge, and then he would back off. Just when I thought he would finally make me cum, he stopped again and Nina joined the show. It was such overstimulation. I haven't had that many sensations happening at once and it was incredible. Nina surprisingly took time to warm my asshole up with her fingers and then Pete did the deed. And it was amazing. I actually squirted more than I ever have before from getting fucked in the ass. It was uncontrollable and just this incredible release. I think I actually passed out after that. It got to a point that I was not really in a conscious state. I just was just in a constant orgasm."