Tooch and Squint
written by:
Lydia

Please enjoy this story responsibly. Men should make sure they have tissues handy and women should make sure the chair they are sitting on will not be stained too easily. **********

"Squint, move your butt, we're going to be late."

"Joseph Antonio Tuccinieri, watch your mouth."

"I'm sorry Mama S." Joey replied as he hung his head in shame at having used the word ‘butt' in front of Mrs. Squintizerra. He called her Mama S. because she was like a second mother to him. His parents had been friends with the Squintizerras forever and Mama S had the best smelling kitchen in the world. The only people who called Joey by his full name were Mama S and his own mother. Everyone else called him Joey; well almost everyone.

"Hold your horses, Tooch. It's the first day of school not time for mass. We can be a few minutes late." A voice called down from the bathroom. Tooch, pronounced like pooch, was the nickname given to him by Mary Angela Squintizerra; his best friend since birth (she was a week older than him). Mary Angela was known to her friends as Angel but Tooch called her Squint. Most people assumed that the nickname Squint was a shortened version of Angel's last name. A few, very few indeed, knew that when Angel was born she had an ocular disorder that caused her to squint excessively. Surgery solved the problem before she was school age but it was a private joke that hurt no one so it was going to be Squint forever.

"So, Mama S, the fact that she's late must mean she's trying to look pretty. Who's the boy?" Tooch asked.

"First of all Joseph, my Mary Angela is beautiful. She doesn't have to TRY to look pretty. Second of all, it's some football player named Jackson. What kind of name is Morris?"

Tooch laughed. He knew that Mama S wanted Squint to marry a nice Italian Catholic boy and her question was about ethnicity and religion not an attempt to mock the boy's name.

"Don't worry Mama S, Morris is a nice Jewish boy so I'm sure his parents are equally unhappy about the two of them as you are. It's probably just an attempt to make you crazy. I'll keep an eye on them."

As Mama S thanked him Tooch heard footsteps and finally Squint appeared. Tooch, who barely thought of Squint as a girl, had to admit that the small amount of makeup and the extra brushing of Squint's long jet black hair gave her a little sparkle. Squint kissed her mother goodbye and the two kids headed out to Tooch's car.

"Squint, you're wearing makeup. Is this for Morris or have you already dumped him and are you out trawling for boys?"

"Can you ever stop being a jerk? Morris and I are still going out; it's been nearly a month and I do not ‘trawl' for boys. They flock to me."

Actually, although it was meant as a self-deprecating remark, since Squint thought of herself as a tomboy and not very attractive, the fact was that Squint was quite attractive. She just tended to hide it by wearing plain clothes and shapeless fashions like overalls. She was slightly tall for a girl, about 5' 9". She had an athletic build from hours on the basketball court. Her breasts were a little big for her taste as an athlete, 36C, but perfect on her frame. But, her most striking feature was her coloring. She had incredible olive skin and jet-black hair without a blemish or split end to be found on her anywhere. Even though she had put on some makeup this morning, she really had no need for it.

They got to school, hugged at the door, and headed off to their homerooms. This was senior year and it was going to be a good one.

Tooch was changing for gym when he heard voices from the next row of lockers.

"Yeah, when I squeeze her tits, Angel lets out this little moaning sound and when I fuck her she lets out these loud groans."

Tooch came around the lockers at light speed. As the group of boys saw him come up behind Morris, they quickly dispersed.

"Shit." Morris muttered as he turned and saw Tooch standing there. Tooch was not football sized like Morris. He was about 5' 10" and well developed with very strong legs from years of shooting hoops. But he had a look that made you fear him when he was angry.

Tooch glared but he spoke softly, so softly that Morris had to strain and lean closer to hear him. The menace in his voice was clear. "I've known you for a long time, Morris, so I will give you the benefit of the doubt. I am confident that you weren't just speaking about Mary Angela but you were talking about some other person named Angela. I know you would never be disrespectful to Mary Angela like you were just being to this other girl. Mary Angela is like a sister to me and no man would ever talk about another man's sister like that in public; would he?"

Morris was big but he wasn't stupid. Tooch was scary just now. "Joey, I'm really sorry. I didn't know you were here. I swear I wouldn't do anything to hurt Ang... I mean Mary Angela. I was talking about a letter in one of those magazines."

Tooch turned around and walked away. Crap, he thought, Squint was a good girl. No way was she putting out for this guy, or anyone. It wasn't that Tooch was a prude or even a virgin. "But, I'm a guy." He thought. The fact that he was a guy who was having sex with girls just like Squint and that it would be hypocritical of him to think that Squint wasn't allowed to have sex seemed to totally escape him.

On the ride home from school the chatter was light. Tooch said he'd meet Squint in 20 minutes at the court for their regular game. Squint and Tooch generally shot hoops at their old grammar school together a few times each week. Tooch had weight and body strength in his favor. Squint had speed and accuracy as her tools. In one-on-one action it generally went in Tooch's favor as he could muscle his way to the easy lay-ups. If they played horse it was typically Squint who won, as her outside shooting was accurate as hell.

They'd been playing for about half an hour and they were taking a water break when Tooch broached the subject.

"Hey, Squint, you and I are friends right?"

"Last time I checked."

"We tell each other stuff. We tell each other the truth, right?"

"Yeah, what's going on?"

"Well, it's like this, you see, well." Man this was hard for Tooch. "How come you didn't ask me before doing stuff with Morris? I mean isn't giving up your virginity kind of an important decision for a girl and shouldn't she talk to her best friend first?"

Squint was stunned. "First of all I didn't give up my virginity to Morris."

"I knew that bastard was lying when he said you'd done it with him. I'll kill him for making up that story and trying to give you a bad reputation."

"Whoa, Tooch, slow down. I did have sex with Morris. I haven't been a virgin for almost a year. What is this all about? You've been screwing girls since you were 16. Do I need to list them for you?"

"This isn't about me. This is about you. When your father got sick and died when we were 12 I promised him and your mother I would look out for you. Good girls don't put out and my Squint is a good girl."

Squint was hurt and angry. "You fucking hypocrite." She was yelling.

Tooch visibly blanched at her use of the ‘F' word. Squint never spoke like this either to him or around him.

"Are you going to tell me you never fucked Katy McGregor or Lacy Vincenzi or you never gave or received oral sex with Dominique Picioccio? Are you going to stand there and pretend that you got a hand job from Alexis Marconi in the backseat of your car last week? So, if it's okay for you to fuck, suck, and cum all over town why can't I?"

"Squint, calm down, I'm sorry, I just, you know, please stop using those words. I mean, I never thought of you that way. Ok, it's just sort of a shock to find out that you've got some experience. But, I never told you about any of those girls, how did you find out?"

Now Squint was amused. "You think guys are the only ones who talk in the locker room? Didn't you wonder how come Lacy practically jumped your bones a week after you fucked Katy? Katy was telling everyone how big you were and how she liked your circumcised penis and Lacy had only been with Tito and he isn't circumcised so she wanted to give it a try."

Tooch was more confused than ever. He never thought the girls would talk. He figured they wouldn't want the other girls to think they were easy so they would keep things to themselves.

Squint wasn't done. "Oh, for the record, I don't remember you checking with your best friend before having sex either. Now, can we get back to basketball?"

Tooch played but not well. This was all confusing and he was too distracted to play well. Squint wasn't a little girl and he wasn't her father or even her big brother; this was a whole new perspective for him.

Tooch took a long hot shower that night and slept soundly. In the morning, Squint came out of the house as he pulled up so he didn't have to get out of the car. As she walked to the car, Tooch couldn't help notice her tight short-sleeved t-shirt with the scoop neck did a nice job of highlighting her firm breasts. The jeans she wore were tight enough to show she had well formed hips and the inch of flat stomach that showed above her belt where her shirt fell short reminded him of how athletic she was. However, when she turned to wave goodbye to Mama S. it was the tight fit across her ass that made Tooch miss a breath.

As Squint plopped into the front seat a slight scent of lilac filled the car and Tooch hesitated before putting the car in gear.

"Are we okay?" Squint asked him.

Tooch smiled back at her, patted her knee, and said, "Always!"

It took a couple of days for their routine to take things back to normal. They didn't speak any more about either of their sex lives. Secretly, Squint was wondering if she and Tooch had a chance together. She wasn't sure if their friendship could survive a romance. They had always kissed, since they were kids; it was an Italian thing. But it was always close mouthed. They had seen each other naked when they were 9 years old. That little game of doctor was never discovered. If it had, they'd probably both still be saying Hail Mary's and Our Father's into their 30's. They'd spent many nights together as their parents often vacationed together or played cards into the wee hours so the kids would sleep over rather than have to go home in the middle of the night. At the same time, Tooch was having impure thoughts about Squint. He would try to push her out of his mind when he was alone in bed but somehow no matter who he started his fantasy with in the end it was Squint's face and body he would be seeing in his mind as he spilled his seed. No matter how good she looked, he knew he could never be with Squint; too much history. Squint wasn't just a girl.

Tooch logged on and checked his email. There was an email from an address he didn't recognize but the subject was Corvette Pics and Tooch loved Corvettes. He opened the email and saw there were several pictures attached so he opened them one at a time. The first one he opened filled his screen with the image of a pair of white cotton panties with the Playboy Bunny Logo right over the sweet spot. It was a close up so that all you saw were the panties so at first Tooch didn't realize there was a woman wearing them. You could only see the slightest amount of flesh above the waist and at the legs the way the picture was cropped. The next photo was the same but a finger appeared to be poised to stroke the bunny's head. The next photo showed the finger pushing the fabric of the panties tight into the girl's slit. That was the final photo. Tooch was hard as a rock and he played with himself and came quickly into a towel. The he looked at the pictures again to determine who had sent them. The email account was an anonymous one from Yahoo. He considered it might be Squint given the recent weirdness, he was even hoping a little that it was. The skin color was hard to tell but certainly could be her but the finger was all wrong. It had bright red perfectly sculpted nails and Squint has bitten her nails all her life. For the first time in a while, Tooch's dreams were not about Squint but about his mystery exhibitionist.

The next morning, Tooch double checked Squint's fingers to confirm that she still bit them and he was right; short nails, clear nail polish.

They played basketball that afternoon. Squint was losing by a fair margin and Tooch was taunting her.

"Hey, I tell you what, let's play to 15. If you win I'll do your history paper due Friday. If I win, I get to drive your car from Thursday after school until Saturday dinner."

Tooch was waffling but when Squint accused him of being afraid of a little girl and a sissy he agreed to the bet.

Tooch quickly got off to a 3-0 lead. When it got to 5-0 Squint called a timeout and offered to raise the stakes. If Tooch won he would also get $20 cash but if Squint beat him he had to let her use the car and buy her dinner on Saturday night. If Tooch had been smart he would have recognized a hustle when he saw one; Tooch wasn't that smart.

Before they resumed play, Squint took a drink from her water bottle and then calmly pulled her sweaty t-shirt over her head leaving her standing in her sports bra and her gym shorts that suddenly looked much smaller and tighter to Tooch.

"Wow she has a nice body." Tooch was smart enough not to say out loud as he could hear his heart thudding in his ears. What he did say was "No fair you can't take your shirt off."

"Why not? You do it all the time. You gonna play or stand there looking stupid?" And she tossed the ball to him.

I'll spare you the details but it was ugly after that. Every time it seemed that they might touch or bump into each other Tooch backed off, afraid to feel her skin on his. Squint won 15-6. Squint pulled her shirt back on before kissing him on the cheek and whispering, "I'll really enjoy opening her up and seeing how fast she can go."

That evening when Tooch checked his email he had another from the picture person. He noticed it was sent during the afternoon while he was playing with Squint. This time there were no pictures just a message.

"If you promise not to play with yourself between now and Friday, I will promise you a great orgasm on Friday night. Be at home and be alone! You should check email at 10 pm."

His cock was at attention and while he was sure there was no way this girl could know for sure whether he jerked off or not, he decided not to take the chance. It was Wednesday; another 2 days wouldn't kill him.

Thursday morning Squint reminded him of the wager as she got in the car. In the afternoon, Squint climbed into the driver's seat and Tooch took his place in the passenger seat. This was the first time Tooch had ever let anyone drive his car; he had never even sat in the passenger seat before.

"So, Tooch, since you have no wheels do you want me to pick you up tonight and we can go grab a late snack at Denny's or something?"

Tooch had no intention of going anywhere tonight. His parents were away for the weekend, he was expecting a surprise at 10, and he had a near-constant erection between thinking about the girl with the bunny panties and noticing how hot Squint really was.

"Come on, you're making me feel guilty for taking your wheels. Maybe I should come over and we'll watch a movie on the big screen TV. I have something I have to do at 8 but I could be at your house by 9 or so. I can even grab a pizza."

Damn, suddenly she's got a touch of guilty conscience for using her body to win the bet and Tooch definitely did NOT want her coming over and screwing up whatever was going to happen.

"Listen, I am okay with you winning the use of my car. I should have offered to let you drive it a long time ago. Go enjoy yourself, just be careful and don't hurt yourself." Tooch kissed her goodbye and went home alone to wait for his mysterious girl.

As it got later, Tooch became more impatient. He was watching the clock. He took a shower around 9 to kill some time. The warm water and the soap were almost too much and he almost stroked himself off but he came to his senses and stopped. Now it was a few minutes before 10 and he was sitting in cotton shorts at his computer. The clock downstairs chimed 10. He logged on and checked his mail; nothing. He waited 2 minutes and checked it again; still nothing. Tooch was beginning to think the whole thing was a hoax after 10 minutes but then it came.

"I hope you did as I asked and saved your sticky stuff for tonight. Go downstairs to the back door. There is small paper bag between the door and the screen. Bring it up and open it and then lie down on your bed with the contents. Don't touch yourself. I will call."

Tooch ran down the stairs, ripped open the door, and grabbed the bag. He slammed the door, ran back up to his room and removed the familiar looking white panties with the bunny on the front. They were damp to the touch and a musky odor escaped when he opened the bag. His cock had been hard in anticipation. When he opened the bag and saw, felt, and smelled his gift it got even harder. As he lay down on the bed, his phone rang.

"Do you like your gift?" A soft feminine voice whispered. It sounded a little like Squint but it was hard to be sure.

"Yes."

"I fingered myself hard to get them all juicy before I dropped them at your door a few minutes ago."

"Who are you?"

"Joseph, my name isn't important but if you must call me something call me Lucy my last name is Furr. Now, take your shorts off and lie back down with my soaked panties wrapped around your hard cock."

Tooch did as he was told. He was trying to identify the voice. It really did sound like Squint but she said her name was Lucy.

"Joseph, I'm going to do most of the talking, you lie back and enjoy yourself. Please tell me when you spurt and I want you to get as much of your cum on my panties as possible. Is that okay?"

"Yeah." "I want to tell you that I am lying on my bed with nothing on. I have nice round tits but the best part is that my nipples get really hard and stand out like pencil erasers when I am aroused. Right now, I am picturing you lying naked with your hand wrapped around my panties and my panties surrounding your nice hard cock. Go ahead and stroke up and down a couple of times but not too much yet. I am rolling my hard nipples between my fingers. I like to do it hard so it hurts a little but then it sends a jolt to my pussy. I really love to play with my tits but I like some moisture on my nipples so I'm going to suck on my finger and lick it and then circle my nipple with it. Oh, yeah, wow, that feels so good. Why don't you do that to yourself too? Does that feel nice?"

Tooch did exactly as he was told. He had never tried playing with his own nipples before. It was like finding a new friend; it sent a tingle to his cock that made it jump slightly. He let out a low moan that told his caller that she was getting to him.

"You like that. The best lubrication to use on my nipples is pussy juice. I like the slick feeling it has. I think I should reach down and slip a finger into my slit. Do you want me to slip a finger into my pussy, Joseph?"

"Oh, yeah do it, push your finger into your pussy, Lucy."

"Huhh, huhh, oh yeah I love a finger in my pussy. I like to work it in and out like a tiny cock and then slip in a second finger to help scoop out my juices. I am sliding my fingers up from my mound over my tummy and up to my breasts. I can see a slightly shiny line of my juices. I need more so I am shoving those two fingers back into my pussy as I imagine what it would be like to have your cock inside me driving me toward my orgasm. Slowly stroke your cock like I was sliding up and down on your shaft. Oh yeah baby. My fingers are soaked. I am rubbing my juices all over my tits, how I wish you were here to lick them clean. Now I am sucking my fingers. I love the taste of my pussy juices. I bet if you were here you'd lick my pussy. Would you lick me until I came on your face?"

Tooch was stroking a little faster now and he was more turned on than he had ever been before. The combination of not knowing who was doing this to him along with the vivid imagery was wreaking havoc with his senses.

"God, yes, I would lick your pussy and clit until you screamed my name."

"I am really close to cumming. I want you to cum with me. I am stroking my clit faster and I have two fingers in my pussy now and I am playing with a nipple. Stroke faster and make sure to fill my panties with your cum. Oh, fuck yeah, oh fuck yeah, I want your cock in my mouth filling me with your cum. I need to feel you fucking me harder oh god yessssssssssssssssss."

As her screams increased and her orgasm built so did Tooch's. He let out a yelp that he was cumming as he shot load after load into the panties wrapped around his cock. Each spurt seemed as strong as the first until gradually it subsided and he felt himself start to breath evenly again.

"It sounds like you shot a lot of cum into my panties. That was good. Did you like it?"

"Oh, god, yes I enjoyed it. When can we meet?"

"Silly, Joseph, we've met. But, I'm not the good girl you think I am and I wasn't sure you'd have sex with me if you knew my real identity."

Tooch was getting hard again. The voice was familiar even as a whisper. "But you said your name is Lucy."

"That's not my real name. Say my full name aloud, if you figure it out by the time I count to 20, I will let you fuck me for real tonight."

"Huh, Lucy Furr....Lucy Furr...."

"6...7...8...9..."

"Lucy... Furr...Lucy Furr... shit, what am I missing?"

"12...13...14..."

"Lucy Furr...Lucifer...Lucifer..."

"17...18..."

"Lucifer...the opposite of Angel. It is you Squint."

"Not Squint, she's Tooch's best friend. I'm Angel and Angel is Joey's hot lover." Mary Angela walked through the door wearing nothing but a smile with her cell phone pressed to her ear. As she climbed onto the bed, she closed the cell phone and removed the cum soaked panties from Joey's hand as she lowered her mouth over his hard-on.

As Joey looked down he realized she was right. Squint and Tooch could never be lovers but Angel and Joey could.

The feeling of her long hair tickling his thighs as she sucked his cock was heaven on earth. Joey reached down to stroke her hair and face as she moved her tongue over his cock and took almost his entire length down her throat.

"Oh, Angel, it feels so good. You are the sexiest girl in the world."

He pulled her up so they could kiss and then Joey rolled Angel onto her back. He slipped two fingers easily into her dripping pussy and then scooped out her juices and spread them over her nipples.

"I believe you asked me to clean your pussy juices off your tits." He said as he lowered his head and pulled one of her nipples between his teeth. Joey then sucked and licked both of her nipples as her breathing quickened and he could feel her hips arching beneath him.

"Oh, fuck, Joey, that feels so good. I can't believe how good that is. I may cum from just having your bite my tits."

That was all the incentive Joey needed to re-double his efforts. Angel was beginning to arch her hips way up every time he pulled on her nipple either with his teeth or lips or with his fingers.

"Fuck, Joey, I'm cumming Joey, uhh, uhh, uhh." Angel was bouncing on the bed and panting as she clenched her fists and curled her toes.

Joey watched as her chest flushed red and her grunts became a long scream of ecstasy. As she seemed to be coming down from the orgasm, Joey reached down and slipped two fingers up and down her slit making sure to rub more of her juices over her clit and occasionally slipping his fingers deep into her pussy. Angel responded immediately to the direct attention to her clit by screaming "Oh, fuck I'm cumming again, holy, fucking god." This time her hips were thrusting up against Joey's hand and trying to squeeze his fingers every time he inserted them. Her panting and moaning just kept getting more frantic. "Oh god, yes, fuck me with your hand, shove it in me, fuck yeah, oh god, I can feel it dripping into my ass, oh fuck. Aieeeeeeeeeeeeeeeeeeeeeeeeeeeeeeeee."

The scream was so loud that Joey wasn't sure for a second if it was pleasure or pain but the way she grabbed his wrist and pushed his fingers deeper into her pussy told him all he needed to know.

This time Angel nearly passed out so Joey turned things down a bit but he continued to gently play with Angel's breasts and pussy lips. His own cock was so hard it was twitching and he could see some pre-cum leaking out the tip.

Angel rolled over slightly and said to Joey, "On your back."

Joey rolled over and Angel straddled his hips. She took hold of his hard cock and gently stroked it. As she continued to stroke it slowly and rub the head around the entrance to her pussy she asked, "Are you ready for the best fuck of your life?"

Joey just nodded.

Joey watched as Angel rose up a little on her knees and then slowly guided the tip of his cock to the entrance to her soaked pussy. She lowered herself slowly as the head penetrated her pussy she lowered herself quickly all the way down. Joey couldn't believe how much he loved the feel. It was like a warm soft glove of honey had surrounded his cock.

Angel began to slowly ride him up and down and then she slipped all the way off and quickly slipped three fingers into her sopping pussy. She worked them around and then pulled them out and leaned forward to slip them into Joey's mouth. He hungrily licked her juices clean as his cock rocked gently against her outer pussy lips. Joey tried to push up but without any help it was impossible to get his cock to penetrate.

"It feels like someone is impatient. Do you want my pussy wrapped around your cock again?"

"God, yes."

Again, Angel slipped Joey's cock into her pussy and lowered herself so he was fully inside her. She sat up very straight and held herself very still. Joey and Angel locked eyes and then he felt it. Somehow without moving, at least Joey couldn't see her moving, Angel was making her pussy squeeze and contract around his cock. It felt like he was being milked by an expert as it tugged from his base to his tip in a nice rhythm.

"Oh, god that is unreal. How do you do that?"

"You can thank a guy named Kegel for that."

"Oh, fuck, Angel, I'm gonna cum, quick get off so you don't get pregnant."

Angel just worked her muscles faster and harder as she said, "relax, I'm on the pill."

Then as Angel rolled her hips forward and began to work him up and down she leaned forward and began to bite and suck Joey's nipples.

"Fuck, yeah, fuck yeah, I'm cumming, I'm going to cum in your pussy, fuck yeah." Joey grunted and humped his hips upwards as he shot his second load of the night deep into Angel's pussy. When he stopped spurting Angel slipped his softening cock out of her pussy and slid down to lick his cock clean.

"Oh, Angel, I love you so much, you are incredible. Fuck I came so hard. I can't believe I am hard again." It was true. Angel's blowjob was quickly bringing Joey back to life.

Once he was hard again, Angel raised her head and looked up at Joey. "Joey, there is something I have never done with another person and I want to try it now, with you."

"Anything." "I want you to fuck my ass. I want you to put your cock in my ass and pound me until you cum."

Joey thought she had a very hot ass so it took about a nanosecond for him to agree.

Angel knelt forward with her head on the pillow. Joey massaged her pussy and used their combined juices to lubricate Angel's small brown hole. Joey had seen this in porn films and read about it in magazines but he'd never done this before. He worked his fingers around her sphincter and slowly slipped one finger in.

"Oh, god, that is so tight. It hurts but it feels good too. Push it in further."

Joey worked his finger further into her and he could feel her loosen slightly as he heard Angel let out a long slow breath. He continued working his finger in and out until Angel asked him to fuck her with his cock. Joey took a quick dip into her pussy from behind to add a little lubrication to his cock and then he pressed the head against her ass.

Slowly he pressed until the head passed the rim.

"Oh, fuck that is so full feeling." Angel tried to relax as Joey's cock filled her ass. As he pushed in the pain turned to pleasure and within a couple of minutes Angel was thrusting back to meet Joey's cock. "Oh, fuck me fuck me hard."

Joey was getting more excited with every passing second. This was tighter than any pussy he'd ever been in. He began to really fuck Angel's ass harder and faster as Angel reached up between her legs and started to finger her clit.

"Fuck me faster harder."

"Fuck, take my cock, fuck yeah, I love your fucking ass. I'm going to pump your ass full of cum." Joey was getting into it and Angel was getting close to cumming as her fingers flew across her clit.

"Oh, fuck faster, I'm about to cum, shoot me with your cum. Oh fuck, oh god, fuck yeah..................FUCK!" Angel came with an explosive fury, which sent Joey over the edge as he bucked and shot his cum into Angel's ass before they both collapsed on the bed.

They rested for a while and decided to shower together before Angel had to go home. When Angel went to get dressed she took the soiled panties and pulled them on. "I think I'll sleep in these panties tonight."

Joey and Angel kissed deeply and passionately but they both knew better than to let Angel miss curfew.

As Angel reached for the door to leave she turned and said, "So, I hear Tooch is taking Squint out for dinner tomorrow night. I think it would be great if Angel and Joey came over here for dessert."