Top Twenty #20

The names have been changed to protect everyone involved but the event did happen.

#20: Cheryl

A long time ago, back in college, I met Cheryl (not her real name) at an off campus house party on Del Playa street. That's the street in Isla Vista, right on the ocean. She was with some other girls that I knew and we started talking while drinking keg beer and doing an occasional shot of tequila. Cheryl wasn't normally my 'type'. I found myself most attracted to slim, almost skinny girls with a tight ass and slim legs. Cheryl was maybe five foot five and definitely had real curves, she wasn't fat, but she didn't have an athlete's toned muscles and she certainly had tits. Big, round, full tits that were impossible not to marvel at, and tonight they were on full display as we chatted at the party.

Cheryl wasn't Delta Gamma hot, she probably weighed about twenty pounds more than the blonde DGs I knew, but the pounds were well distributed, especially on her chest. She was pretty, with a round shaped face round, full lips and a little nose. She had blonde hair that fell below her shoulders and mostly matched her eyebrows but looked to be lightened a little. She was also very fun and flirty with a big personality. It wasn't hard to keep up a conversation between the two of us and we seemed to stay near each other while mixing with the eighty others crammed into the kitchen, living room and balcony of the duplex house we were at.

Two hours later, we were dancing in the living room to a party mix playing from the stereo and then kissing on the front balcony as we waited our turn to pump the keg and refill our red cups. After that beer, we left the party together, slipping away from her friends and a few of my lacrosse teammates and walking down the street towards my house.

We stopped a block away from my house and joined another party, this one just eight houses from my duplex and on the oceanside of the street. A long, bowling-alley shaped two story duplex hosted an open keg, about 70 college-age students on the precariously perched balcony that overlooked the ocean and inside the house. We sat down at the kitchen table and joined in a quarters game for a bit.

Cheryl was one of those girls who rolled the quarter off her cute little nose, letting it bounce off the table and into the shot glass. She was good, even when drunk, hitting 4 or 5 into he glass on each turn and handing out commands "drink. drink. drink" to others around the table. Her technique required that she lean forward over the table and that gave everyone else a great view of her big, luscious tits. I think it could have been why she adopted the technique because it put all the focus on her best physical asset.

She was wearing an off-the-shoulder top that scooped low along her chest and went down over her ass, paired with a pair of black leggings and flats. When she leaned over to run the quarter down her nose, the top exposed her cleavage and the top bit of her white lace bra.

My quarters technique was more conventional, I held the quarter with my thumb and index finger and bounced into the glass. I was also very good since my roommates used playing quarters as a way to down a few beers before heading down D.P. for a night out. I was on good form that night, making several shots each time my turn came up.

We left that place after going outside for a beer refill and geting distracted by making out on the balcony as we waited for our turn at the tap.

Someone said, "Get a room". And I broke the kiss and grabbed her hand, taking the stranger up on his excellent suggestion and also realizing that neither of us really needed another beer.

As we left the Zanadu house, she asked, "Where next?"

"My place, it's just down from here and I pointed past the cracked asphalt parking lot we were standing in at a big tree down the street that stood in front of the duplex I lived in.

"Ok." was all she said and we walked a half block down the street past tens of other students doing same thing, party hopping on D.P.

When we got to my place, I opened the unlocked front door next to the driveway and let her go first up the inside flight of stairs that led to my second floor duplex. It was a two bedroom place upstairs with the identical layout downstairs, a square floorplan with a living room and kitchen facing the street and two bedrooms and bathrooms behind the stairway that bisected the upstairs duplex. I shared it with three other guys but when we got back at midnight, none were home yet.

I took her into the living room, got us plastic cups of water from the Sparkletts water cooler and led her back to the bedroom. I put a sock on the door handle to let Tom know i had a guest, and closed the door, set the waters down on the night table and started to kiss Cheryl as we fell onto my double bed.

Cheryl was a great kisser and we were making out heavily on my bed as our hands roamed every place we hadn't yet gotten to while kissing at the party. Cheryl's ass was bigger than I like, she was a size 8 or 10, but she had a huge pair of tits that more than made up for her chunky caboose. I grabbed her ass and she moaned as I ran my hands all over her butt as she squirmed on top of me while sucking on my tongue that I had pushed into her open mouth.

She kissed hungrily back at me, using her lips to capture my bottom lip and gently sucking on it before moving her mouth over mine again and accepting my tongue as i pushed it into her open lips. My hands left her ass and traveled up her waist and to her back, then forward to her big, grapefruit-sized tits. They were the biggest ones I'd ever handled, probably 38E and I cupped them and fondled them through the lose top and she ground her pelvis down onto my hard cock, still stuck inside my jeans.

"Will your roommate be back soon?" she asked in my ear.

"Maybe, but he will sleep on the couch." I said.

"Are you sure?" she said, looking at me hopefully.

"Positive. We have this room to ourselves." I said, squeezing both her big, round orbs for emphasis.

"Good.." she said as she scooted up slightly and pulled her top away from her front where it was caught between her legs and my pelvis. That made it easy for me to get my hands up her oversize top and squeeze her big melons and run my hands over her lacy, underwire bra. I moved my hands under her top and she sat up and tilted her hips back as she steadied herself with her hands behind her and let me play and massage her tits.

"mmmmm, feels good!" she said as I pulled gently on her nipples.

When I cupped her tits again I felt the plastic clasp between her bra cups and I got both hands on the clasp and unhooked the front clasp and let her bra fall away from her body and land on my thighs behind her. I grabbed onto those big, round tits after they came free and massaged them with my palms under her top. I could feel her fat, erect nipples on my fingertips as I worked my hands around her massive orbs.

I pushed up on her shirt and then grabbed the bottom of it and began pulling it up over her tits. She sat up and took hold of her top and pulled it over her head, and her big, natural tits stood out proudly and hung suspended high on her chest like only youthful tits can. She scooted up onto my stomach, leaned over me and pointed her tits down at my face, stopping her body with her bent arms so that her nipples were just a few inches from my nose and mouth.

I tilted my head back to look into her eyes and said, "They are perfect, round, big and hard." and she smiled.

"Yes, I know. Guys have been asking to touch them since I was fourteen"

I got to work, sucking, kissing, caressing and fondling her big, soft chest-pillows as she cooed and moaned encouraging noises.

I continued the dialogue between slurps and sucks, "Sooo big and perfect. I love these big tits, I've been staring at them all night, hoping to suck them like this."

"Mmmm, yes, I know! Guys love my 'man catchers', and I don't mind the attention." she said, grabbing the sides of her tits and pushing them together as i sucked on one, then the other. "it can get old when guys just stare at my tits, but you did pretty good at keeping your eyes on my face... Except when we were at the quarters table."

I chuckled. "You noticed?"

"I noticed you and every other guy looking at my tits, my bra was showing, wasn't it? I can't help it, it's the only way I can sink the quarter. Otherwise I suck."

I was slurping on one nipple as I grabbed both of them and pushed them together so that both nipples were an inch or two apart.

She moaned and moved slightly forward "I love having them sucked. I love pressing them into a guy's face so he can kiss and lick them. They've always been sensitive, ever since they started getting big.".

"You were fourteen?" I said, pausing for a moment and then licking the underside of both massive melons.

"YES! Oh, right there. Fourteen. By the time I was fifteen, they were 36D. A new ninth grader in high school with these on my chest. I had a senior for a boyfriend by the end of the first week of school. He gave me rides home from school after the first week of class in his camero and he was the first guy to play with them a few weeks after school started."

She was lost in her own world, drunk reliving her first HS crush as I kept up my assault on her perfect tits.

"Did you let him do other stuff?" I asked, since she was clearly enjoying the attention I was paying to her tits while she told me about her first boyfriend.

"No, that's why he broke up with me. I would only let him take my shirt off. I wouldn't let him fuck me, and I thought blowjobs sounded gross."

"Oh really?" I said, hoping she wasn't still grossed out about sucking cock since that was next on my plan for tonight.

She laughed lightly, "Don't worry, I don't still think giving head is gross." she said with a wink. She slid her leg off my hips but kept her tits in my face as she reached over and stroked my bulge in my jeans. "This feels nice and big. Can I see it?" she cooed.

"Of course." I said and took my hands off her tits to undo my jeans.

She stopped my hands, putting one back on her tits. "Keep these where they belong, on my tits. I can handle this.". She undid the five buttons of my button-fly Levis and reached into my underwear to pull out my stiff, 7 inch pole.

I took a hand off her tits and pushed it into her black leggings and down onto her trimmed muff, feeling for her pussy lips.

She curved her back and moved a little closer so I could get my index finger in between her swollen pussy lips.

"So you changed your view on blowjobs?" I said hopefully.

"Nice." she said as she grasped the shaft and ran her thumb over the tip. "I didn't suck Mark, but my next boyfriend Todd, he was also a senior and was a little more patient with me and loved my tits even more than Mark did. At the Christmas dance, he was so charming in his tux and I was also determined not to lose him like I did Mark.". She said as she stroked my cock gently as I sucked her nipples and held up her big tits with my hands.

"So for a few weeks before the dance, my girlfriend helped me practice giving head one night and then I practiced every night before bed with a hairbrush handle."

She looked back at me. "you want to hear more?"

"Sure, this is interesting." I said.

She smiled a little naughty smile as i found her clit with my index finger and started to circle it lightly with my finger tip. She hunched her hips down onto my finger, increasing the friction and the reach of my hand. "Well, it's pretty simple, after the dance, at a hilltop parking spot... I gave my first ever blowjob. Turns out, thanks to the hairbrush, I was a natural at it and thanks to my big tits and my eager little mouth, I kept Todd as my boyfriend through the school year and until the next Fall, when he went to college.".

She pivoted on her knees, presenting her legging-covered ass to me and moving her attention to my erect cock to examine it before looking back at me. "Todd was my first. And he also played lacrosse. I think it's why I like lacrosse boys so much.". And with that she started licking and sucking on the head of my cock, no more talking as she focused on showing off her five years of experience at giving head. I pulled her tight leggings down over her plump ass and down to her upper thighs and her panties clung to the leggings and went down with them, exposing her pinks, swollen, puffy pussy lips.

Her ass didn't sag, but it was big and round as I reached under her and rubbed three fingers up and down her slick pussy lips. She moaned onto my cock as I slid my digits up to her clit and then into her fleshy pussy lips and then back down to her wet, pink hole. She moved her lips off my cock and scooted down the bed and put my cock between her tits as she held them together and stroked them onto my spit-covered cock.

"Todd loved it when I used my tits on his cock." she said. So has every guy since. Do you like it baby?".

"Love it!" was all I could say, fearing an early eruption if I started talking about the feeling of her big, fluffy tits jerking my cock. I now knew why some guys were 'tit men' the feeling of my cock crushed between her mounds was exceptional and I focused on not cumming any time soon.

I had practiced too, spending long amounts of time in my bedroom during my high school years and rare days in college when i knew I wouldn't be walked in on, humping my pillow and working on my ability to surpress my orgasm. I didn't like jerking off with my hand, I much preferred humping my pillow and getting dangerously close to orgasm before using my PC muscles to prevent ejaculation. I was good at it and could almost always fuck a girl for any length of time she preferred, a five minute quickie, or 40 minutes of pussy-pounding that required a few squirts of lube to keep things moving together nicely.

My control was being tested by Cheryl as she applied her lips to the tip of my cock without taking her titan rack off the shaft of my dick. I could hear and feel her sucking the tip, alternating soft and hard sucks on the sensitive helmet of my rock-hard cock.

I slid two fingers into her wet pussy lips and found her opening, sliding the middle finger in an inch, followed by by index finger. She was sopping wet inside, her juicy pussy clinging to my fingers as I pushed them deeper. I felt her tense and squeeze her pussy around my fingers as they reached maximum depth and I felt her lips choke down and take a second inch of my cock into her hot, talent mouth in response to my fingers diving deep into her tight snatch.

She pulled at her leggings stuck on her upper thighs for a moment, succeeding in getting them to her knees before releasing my cock from her mouth long enough to say, "Get them off. My leggings, I want them off." she said as she then reached down and tugged at my jeans.

The two of us pulled each others bottoms off, squirming around to lift up off the bed while the other tugged at the pants. We were both pretty buzzed, so it wasn't elegant, but finally I pulled the legging off her left ankle and threw it on the floor. She did the same with my jeans and now I just had on my college lacrosse team t-shirt and she was naked other than her earrings.

Once I had her leggings off, she threw her leg over my ear and put her pussy inches from my face. I took the hint and pulled down on her full ass until my mouth was on her slick, swollen lips and I began to tongue her cleft, causing her to moan as she pushed her lips down my shaft in time to the motion of her hand around the base of my stick.

"Eat my pussy good." she cried as she pulled her lips off my swollen cock. "Make me cum on your tongue while I suck your big cock."

I licked and sucked her clit and busied my fingers inside her open gash, finger fucking her noisily as I kept my mouth on her swollen nub until I felt her hips begin to buck against my fingers and her lips came off of my cock as she sat up part-way.

"Eat my pussy... So close... make me cum... sooooo good, you suck my pussy soooo good. Make it cum... gonna gush all over your face... soon. Very soon. Here it comes, cummmming!!! Cumming on your face! Yes! Yes! Yes! Oh god, don't stop, oh yea, lick it good.". Then she just panted as she came down from her orgasm and I let up on her wet hole, giving her a chance to regroup.

She just sat there, straddling my face for thirty seconds before moving her knee and uncovering my face.

"mmmmm, that was good, never been eaten like that the first time, usually I have to show em how I like it. You just KNEW." she said, beaming. Maybe it's something with lax players, but you get an A+."

"Glad you liked it. I got a good grade, but do I get some of this?" my hand going to her still puffy slit.

"Yes, if you have condoms." she said eagerly.

"Always Prepared, the lax players motto." I joked.

"Lax players are NO Boy Scouts." Cheryl joked. And I like lax players much better." she said stroking my cock lightly with her hand.

I pointed to the nightstand drawer. "In there."

She opened the drawer, pulling out the box and some lube. "Magnums. Nice. And lube also. You ARE prepared.".

"They fit better, I don't break them like I do the others."

"Mmmm, don't want em to break, definitely not." she said, pulling three wrapped condoms out and tearing the package of one open and extracting the thin latex ring from the package. She grabbed my cock, licked and sucked on the tip for twenty seconds to make sure I was in the 1A position and pushed the condom over the helmet and then down the shaft, leaving a space up top for my cum to shoot into.

"Not your first bone wrapper." I joked.

"Nope, in HS, I couldn't get on birth control till I was almost 18, I got used to wrapped weasels. I started putting one on Todd one day and from then on, he always had me put his 'raincoat' on for him. I've kinda done it ever since. I like knowing it's on right." she said

I sat up and moved to my knees, getting behind her and sliding my wrapped cock along her wet lips.

"Doggie first? No missionary?" she asked

"Doggie first, don't worry, I'll flip you over and do you that way too."

"whatever you say." she said as she reached up under us and guided my cock onto the entrance of her pussy. I let her put the tip in and held her wide hips as she pushed back against my steel and latex shaft as we both felt my cock slide up into her snug box. Once the head had nestled nicely inside of her, I pushed gently, feeling her pussy ease open and my cock dive further into her velvety depths. The condom reduced the sensation, making it easier to fuck her without fear of cumming before I wanted to. I pulled out until just the tip was inside and pushed again, driving most of the shaft into her hole as she started to moan.

"ohhhh, yes. Work it in me, make me take it all, Magnum. Mmmmmm, it is nice and big inside me." she said flexing her pussy and squeezing my cock as I buried all but an inch inside her from behind. "now you can fuck me good,

Magnum, it's all inside. Grab my big ass and fuck meeeee." she said as I grabbed her ass cheeks and pushed in and out, making each stroke a little harder and deeper as I began to fuck her good.

I heard the entry door squeak open and then rattle shut as two pair of heavy footsteps made it up the stairs. "Damn, he's in there with a girl." Tom said.

"Uh huh." Tim retorted, looks like the couch is your bed." Tim said,

I could hear them move to the living room and I didn't stop fucking Cheryl but she froze until the voices stopped. She took my cock quietly after that, making quiet grunts, but not talking or yelling as she had done when we were home alone.

I leaned down over her and put my mouth next to her ear, "Still enjoying it? I said,