The Deepest Friend-Zone Ch. 04

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Connor walks home the girls talk about his future with them.
3.6k words
3.84
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Part 4 of the 8 part series

Updated 06/09/2023
Created 03/27/2019
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Vanttont
Vanttont
62 Followers

The boys gathered their things and left without much of a peep from their mouths, most like a bit shocked from the experience.

The door closed and girl time began.

"Toonnnnsssss of fun!" Nina said with more energy than one would expect her to have.

"I know, right? Those were great picks. I could do with either of them. Maybe both" Sarah said sounding slightly more worn out but still excited.

"You couldn't handle both, you get too mushy when you fuck. You'd just make sweet love to one of them and lose track of the other." Nina talked down at her.

"I would be fine, thank you very much. I can 'make love' to them both perfectly well" Sarah chirped back

"Have you ever even had anyone in that tight little ass?"

"No" Sarah said innocently

"Well, they would expect you to take it in both at the same time so I'm not so sure you're ready" Nina scolded.

"We'll then get me ready, bitch"

"Woahhh, someone's not miss cute and sweet all the sudden"

"Yea well we both know it's just a look, not what I'm actually like" Sarah said flirting at Nina.

"Ok. We will work on you. I'll have have one of my horsies come by tomorrow for a learning session" Nina said as she picked up her phone to text Pete.

Pete was a guy she had kept around for a bit. He was a guy she met in class who unfortunately was not as well endowed as most of her hookups, but was definitely phenomenal in using the tools he had. Pete and Nina had a unique arrangement in that he got to eat her out every monday morning after their 9am class. He knew that this was after a weekend of her typical escapades and he was turned on by eating a used pussy. Rather often, this turned into a mid morning fuck fest but occasionally Nina would just let him clean her well and leave. Nina even had him come over a few times right after she had finished with another hook up. His skills and equipment would be perfect for getting Sarah ready for what she wanted.

"Yay, Sunday's are great for days of fucking!" Sarah said goofily.

"Yea you're buns won't be saying that Monday but it's ok" Nina retorted as they both laughed. Nina loved selling anal to her friends. It was her favorite and she did not understand why it was not something that everyone loved. She had converted her other roommate Brianna into a chubby anal slut. She now has a boyfriend who loves to have threesomes with her. After her first time being penetrated in both holes at once, she knew she had to have it way more often. Nina kicked off her crazy streak by sharing Pete with her, and then she had a threesome with Pete and his roommate on her own time. Now Nina was hoping she could get Sarah to start off on the same path.

XxxxxxxxxxxxxxxxxxxxxxxX

The walk across campus was a rather miserable one, especially in the cold and all alone. Connor lived as far across campus as possible. The girl's suite was in the ritzy dorm across campus and Connor was in the "temporary housing" that was a fake name for what equated to a huge trailer.

The amount of crazy thoughts going through his drunk head made the walk seem like time travel. He didn't even know if he had been going the right way. Connor had watched a lot of porn in his time, and at no point did anything affect him in the way he was currently distraught. His erection had never gone down since the beginning of the night. The feeling of blue balls was definitely there but the feelings of jealousy about Sarah, the amazement of how brazen those girls were, and sifting through mental replays kept his mind off of the discomfort.

He found himself next to the soccer fields that marked the ¾ way home. Only in his drunk mind would he think that he was compelled to jerk off there, but he was drunk, and this compulsion began upon him. He was horny beside himself, which would get him to do some crazy things, but he would probably just rush home toss himself with some lotion if he was in a sober mind.

The path he was on ran along the back of the bleachers of the home stands. Just about 20 yards up, Connor could see there's was a double gate that had a rather large gap in the middle. It was silly that they even had a chain on it as this was keeping nothing from getting in. Connor thought to himself that this mean he had to do it. He was too horny to continue the walk home.

Connor ducked under the chain between the two gates and was now right underneath bleachers. He quickly looked around to make sure nobody was there to see him sneak in. This was a bit late as he was already inside, but in his drunken state, he was not about to do things the logical way. After seeing the coast was clear, he walked around the long bleachers to reach the front entrance to the seating.

He made his way up the stairs and looked around the stadium. It was eerie to see that literally no one was in sight in such a public place. Everything was so dark that he did not feel so weird sneaking around. Connor decided that the top row, right next to the press box was where he would settle down.

After one last look around the stadium, Connor opens his coat and hastily unbuttoned his jeans, pulled his fly down and pulled his prick out through the hole in his boxers. He wasn't at full mast but he had remained mostly hard through the duration of his walk. There was a deep feeling of relief to finally get his hand on his cock.

Connor was a frequent masturbator. He had a tendency to jack off at least twice a day, sometimes three or four sessions if the opportunity arose. He basically jerked off wherever he could get a private second, sometimes in places more risky than others. It wasn't entirely uncommon for him to sneak a quick rub in a campus bathroom right after class if a girl in class got him going with a short skirt or if his mind went to daydreaming during a boring lesson. His lack of success with girls seemed to make him constantly horny, almost like an itch he had to scratch.

Connor leaned back against the press box and started to stroke his cock up and down slowly to get himself more fired up. He slowly sped up his pace as his cock became rock hard. Connor's cock was about 4 inches long, rather skinny around the shaft, with a relatively large head that looked like a mushroom cap. With each stroke of his hand, Connor's index finger popped over the rim of his cock head due to his strong hold and very erect cock. He loved to focus at the head as this was easily the most sensitive to his touch.

He began to lose focus on his hand as it seemed to become automatic while his mind focused on the sensations. He was feel the sensation in the base of his balls build. He squeezed his love muscles and made the sensation build at a more rapid pace. The urge began to build. His hand jerked faster.

"Quick, step under, I don't see anyone." A male voice said behind him

"Lift the chain, I don't want my hair to get caught" a female voice demanded.

Connor's heart stopped. His cock was throbbing, maybe 20 strokes from exploding. He closed his jacket over him and sat still. He knew he was in the dark and no one could see, but no he was stuck until the coast was clear.

What the hell was anyone else doing here. What were the chances someone else was here to fool around at the same time as Connor? Connor thought that no one else would think this was a good place to have fun.

A couple came around the side of the stands. They were mere black figures as the only light sources around were focused more at the middle of the field. The two hopped the fence with the man helping the girl get over. She was in heels and a dress with an overcoat, but seemed to be rather athletic in the way she navigated the fence.

After they got over, the girl took the guy's hand and started to lead him to the middle of the field.

"Mary-Kate, are you sure this is ok?" The guy said rather loud as if he didn't care to be caught.

"Shhhhh we'll be fine, just get this done quickly" the girl now identified as Mary-Kate said.

This must have been Mary-Kate Conaghan, the star soccer striker for Ballywood University. She was a massive woman who was equally as beautiful as she was tall and muscular. She had just finished her senior season as the leading scorer in the league. It seems she was here to make some memories on her home court.

The man she was with had to be about 6'4" as he had a few inches on Mary-Kate who was at least 5'11" if not taller. As the two of them walked further away Connor knew he was safe from being caught. The couple got just to mid field where a distant glow from a spot light gave Connor a slightly clearer view.

He could see the two start to make make out with the man opening Mary-Kate's jacket and reaching inside to fondle her. She must have been wearing some sort of wrap dress because he seemed to fumble with untying something. Mary-Kate turned toward Connor for a brief second to put her hair into a pony tail, giving Connor a full frontal view of her stunning body.

She was in perfect proportion head to toe. She was very athletic with broad shoulders and muscular arms. Her chest was large for an athletic woman, but she wore it well, looking like a fitness model. She didn't quite have a six pack of abs, but she had two defined lines that ran along each side down to her pussy. Her hips wide, strong, and powerful with defined thighs accentuating her long legs. Everyone on campus knew what she looked like. She seemingly wore her workout regalia everywhere she went. It was hard to keep your eyes off of a 6' knockout of an Irish brunette wearing nothing but her team issue sports bra, Nike Lycra skin tight compression shorts and calf high socks with flip flops.

Mary-Kate laid on her back on the turf and was mounted by the unknown man. Connor could see her round breast peeking past her open jacket and the rest of her body revealed as the jacket fell to the sides on the turf. The man reached down and undid his pants to push them down slightly. His dick was was large enough to be made out from a distance as he grabbed the base and positioned himself to enter. In a swift move, he entered her fully causing her to arch he back and grab his arms that held his chest up.

Connor returned his hand to his cock and began to stroke it once again. Watching the two in the middle of the field was giving him a good show, but his mind kept going back to feeling Sarah's naked body being fucked on top of him. The warm, moist feeling of her sweaty neck and chest against his face. The sound of her breath in his ear as her precious pussy was pounded by a hung stud.

He felt the edge coming again and pulled his hand off of his cock. He opened his eyes from envisioning Sarah. He looked back to the field to see the man jackhammering into Mary-Kate vigorously. He could not hear them from that distance, but Mary-Kate appeared to be mid-moan and cumming from the strong thrusts. Connor matched their pace with his hand and once again came to the edge and stopped, forcing him to buck forward and strain his whole body. He returned his hand to his sensitive cock and decided this would be the time. He could see the man in the field was thrusting harder and getting ready to finish his romp with Mary-Kate. Both men picked up their pace together. The man on the field fell forward and lost his rhythm as he came in Mary-Kate. His hips involuntarily thrust into her as she hugged him close.

Connor could not hold back any more. The feeling built at the base of his balls and his muscles began to spasm. His cock head became incredibly sensitive radiating the pleasure down toward his shaft and nuts. The pressure continued to build, and build. His eyes closed again and the memory of Sarah cumming while lying on top of him played on repeat before his eyes.

Finally, an incredible rope of cum exploded from his cock and landed about 3 bleachers down from him. He continued to rain cum all over his jeans and hand. What he lacked in size, he made up for in volume of cum. He never stopped stroking until the last drop was milked from the head.

Connor relaxed back against the press box and regained his vision after the incredible orgasm. He looked out to see the couple gathering themselves and making their way off the field hand in hand.

"Now that we checked that off the list, let's go in front of the fountains by the admissions building!" Connor overhead Mary-Kate say to the man as the came closer. I guess she was conquering her senior year bucket list which must have included fucking all over campus. Connor thought about how lucky that guy was to be fucking Mary-Kate and getting to be adventurous as well.

The couple finally got out of the stadium and cleared the fence. Connor wiped the cum off his hands onto his jeans as they were already an absolute mess. He closed up his jeans and jacket and walked himself down the bleachers and back out of the stadium. He completed his walk of shame back to his room where he plopped down on his bed face first and passed out in his cum covered clothing. Tonight was too much for him to take in.

XxxxxxxxxxxxxxxxxX

"So how do I ever deal with Connor after that?" Sarah threw out the question of the morning as she busted into Nina and Brianna's room.

"Woah woah woah, it is too early for your bullshit." Nina chirped back

"It is 10 am, get your slut ass out of bed." Sarah demanded

"L O L why are you so bent up, you don't really care about him. If you did this would have bothered you way more last night."

"Well I definitely don't like-like him or even find him attractive, but he is a nice guy and doesn't deserve to be embarrassed like that."

"The little perv probably loved it. He was watching both of us like we were porn stars. I think he'll be perfectly fine."

"True. I mean I could feel his little hard on through his jeans when I was leaning on him. It was cute." Sarah said with a cute smile and a laugh

Both girls laughed at the comment for a minute.

"I should probably make it up to him somehow." Sarah pondered

"Well you're not going to fuck him by the sound of how you feel about him."

"Oh hell no, that won't happen. Maybe like a hand job or something."

"Wait, he has already seen us fuck, and we definitely don't care right?"

"Right?" Sarah answered in a confused and tentative voice.

"Well we really need an 8th roommate for next year and I really hate our female options. Maybe Connor would be the perfect fit? If he is as good of guy as you say, than we have nothing to worry about. He even gets the huge upside of watching our craziness, I can't imagine him saying no." Nina said with building excitement

"A guy as a roommate? I don't think so. How do I tell my dad there is a guy living in our house?" Sarah snapped sassily.

"It's Connor. That's how. When your dad meets him, he will understand."

"Do you think the other girls will be down?"

"If he is as much of a bitch as it sounds like, he is probably less of an issue that any girl we might have to deal with" Brianna chirped in from her slumber. She laid in bed facing out with her boyfriend spooning her, hand holding her right tit.

"I will talk to him. I know Jackie will be fine after the two of them got all excited about video games. We just have to convince the other girls. It will probably be easier if he already said he was interested. " Sarah spoke as she thought out loud.

"Great deal with that tomorrow. Pete is coming over in like, an hour so you should get ready for that."

"Pete?" Brianna perked up. Her boyfriend, Sam seemed to become attentive at the sound of his name as well.

"Yes, Pete. He is going to teach Sarah to take it in the ass. And no, Brianna, you can't join. You and Sam have the room to yourselves all day. We will leave you alone, just make sure to return the favor." Nina answered.

"Fine, fine. Sarah is in for some real fun, I'm a bit jealous! But, Maybe you can get out sooner than later. Sam has been inside me this whole time and I'd like to get the real deal started ASAP." Brianna Finished on a snappy note. After Nina turned her into an anal whore, she started to act all bitchy and demanding like Nina as well. The two of them made for great roommates.

Brianna's boyfriend Sam was short and very chubby just like Brianna, but had a massive cock that was way out of proportion to his height. It came to good use for fucking from every angle and Brianna took full advantage. Sam was maybe 5'6" at most and had a round belly. He was definitely appealing to a specific set of girls with high muscular arms, broad shoulders, protruding pecs, and blue eyes. His cock stood out 9" under his hairy stomach and did a number on Brianna's chubby little pussy and ass. They had an an entirely open relationship, which was made for a fun dorm room between Nina and Brianna.

"Well I need a shower and you could probably use one too, Nina." Sarah said

"That sounds like an invitation" Nina answered with a devilish grin

Sarah turned around and started to remove her Sofi shorts to reveal her shapely ass as she walked away from the room. Nina jumped out of bed naked and chased her into the bathroom where the two girls started to squeal and giggle like teenagers as Nina finished undressing Sarah, then began to violently make out with her.

They got in the shower and had their hands all over each others bodies. Nina started to rub Sarah's mound as they continued to make out. She then pulled away after a minute of deep kissing.

"No cumming. For either of us. I want us to save it all for Pete later." Nina said as she stared into Sarah's green eyes.

"Fuccckkkkk you are killing me. Ugggh!" Sarah moaned as Nina's fingers found their way through her folds and down to her clit.

"I just want you to be so wet for him." Nina whispered into her ear. Nina rubbed her clit a bit harder and faster and Sarah moaned a bit more. Right as Nina felt her back begin to arch, she pulled her hand away.

Sarah yelled "Fuck!" and pushed Nina against the shower wall away from her. "You're a such a cunt!" Sarah said through her teeth with a bit of a grin.

Sarah approached Nina and reached up to grab both of her nipples. She pinched them hard and pulled Nina to kiss her.

"EEE!" Nina yelped quickly before she was shut up by Sarah's kiss.

Sarah kept one hand pinching Nina's left nipple while she reached down to finger her pussy. As always, Nina was sopping wet. Sarah used all 4 fingers together to use large swipes back and forth over Nina's clit. Nina moaned under the kiss and Sarah continued her assault. Nina started to grind her hips back on Sarah's hand, when Sarah stopped rather abruptly and turned the water off.

"Ugh, fuck! Uh I deserved that." Nina said with a bit of a laugh.

"Get the fuck out of here and dry off." Sarah said with a little smile.

The two girls stepped out of the shower to realize they didn't bring their towels in. They walked down the hallway dripping wet back to Nina's room. Nina opened the door to see Brianna on all fours getting fucked from behind by Sam, who had her hair pulled back like it was reigns on a horse.

"Oh hey guys, wanna join?" Sam said to the girls with a smirk.

"Not this time Sam, although it's tempting. You just keep your girlfriend happy today." Nina told him as she grabbed two towels, her sweatshirt dress, and some thigh high socks. Brianna hadn't even acknowledged her presence as she was consumed by their fucking. Nina walked out of the room and closed door. She handed a towel to Sarah.

The girls dried off in the common room and got their clothes back on. They had 2 hours before Pete would be over, so they watched some episodes of Grey's Anatomy and enjoyed their sunday morning.

Vanttont
Vanttont
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4 Comments
AnonymousAnonymousalmost 5 years ago
Too much

Make conner say no please

12356416514a12356416514aalmost 5 years ago
More

I really love the way this started. My favorite cuckold stories are those that focus on jealousy and friendzoning. Love it when a guy has a crush on a girl, but can't date her.

VanttontVanttontabout 5 years agoAuthor
More Connor to come

Glad to hear you enjoyed. I plan to show a bit more of Sarah and her roommates to set up their characters before Connor moves. then the real fun will begin :)

CuckFantasy69CuckFantasy69about 5 years ago
More focus on Connor

I love the set up! I can't wait to see what will happen when Connor becomes a roommate with all these hot girls and is not allowed to have sex with any of them. Jerking off watching them have orgies with hung studs that have much bigger cocks than him. I hope he ends up being teased and dominated by the other girls as they laugh and make fun of him while he watches Sarah get fucked in all her holes.

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