tagFirst TimeSherry Baby, Will You Cum Tonight

Sherry Baby, Will You Cum Tonight


Authors Note: I liked this story line submitted in a reader request so I gave it a shot. The names are fictitious and all characters are at least 18 years of age.


It was the spring of 1959 and Cliff Walters could not believe that he would soon graduate from high school. He had played his last high school football and basketball games and soon baseball would be history as well. Of most concern to Cliff was that he was still a virgin. Unlike his jock buddies he still had not gotten laid in high school. His current girlfriend Susan was a great make out and they petted and played with each other but she would not let Cliff in her pants. She allowed him to unhook her bra and fondle her tits and she let him finger her pussy. However he was not allowed to remove her panties but only pull them to the side to bare her quim. Susan also gave him hand jobs with his cock and balls exposed through his fly.

In 1959 everything was great; the cars, the music, the dances and the clothes. Dwight Eisenhower was the President and Rocky Marciano was the heavyweight boxing champion. Guys hung out under street lamps and sang song hits by a number of artists including one song wonders. It couldn't have been better except for Cliff's virginity. He was enlisting in the Marines after graduation and he did not want to go in as a virgin. Cliff pressed Susan on the sex and she flipped out. They had a huge fight and broke up at least for a week or two.


One day after baseball practice Cliff was leaving the locker room and headed toward the school parking lot when he was approached by a classmate. "Cliff can I speak with you a second," Sherry Borg addressed him.

"Sure Sherry, what's up?"

"I would like to ask you to the Sadie Hawkins dance?"

Cliff was caught off guard and he was in a pickle. He had assumed that Susan and he would go to the dance together but she had not asked him. It was an unwritten rule in school that a boy could not refuse a girl asking him to the Sadie Hawkins dance. He knew that he had no choice in the matter so he agreed.

"Okay Sherry, I know that I have to accept since Susan didn't ask me. I'll go with you," Cliff accepted sheepishly.

"Great, I knew that you and Susan were on the outs and I hoped you would say yes," Sherry beamed.

Sherry turned and walked toward her car in the student parking lot and Cliff watched her. Sherry was stacked with big tits and a big ass. Her ass was bigger than Cliff liked on a girl but it least it was round and shapely. Sherry was one of those 19 year old girls that guys went out with to get all they could off of her. Her mature size was appealing in high school but she was destined to be a cow later in life unless she did some drastic with her life style.

Cliff knew of Sherry's reputation of putting out and he looked on the bright side of things. Maybe he would get laid after all and not graduate a virgin. Cliff got in his car and drove home. He would have to tell Susan what happened and he knew that she would be pissed. Still a rule was a rule and since he didn't have a date to the dance he had to accept Sherry's invitation. The dance was in two weeks and it was unlikely that he and Susan would go out again until after the dance.

Friday night arrived and Cliff picked up Sherry for the dance. Sherry was staying at her aunt's house that night as her parents had gone to the Poconos for the weekend. Her aunt instructed Cliff to have Sherry home by midnight. The dance was more like a sock hop and everyone was dressed casual. Most of the girls wore poodle skirts and saddle shoes with their hair tied up in a pony tail. The dance was a blast as everyone danced to their favorite songs.

Cliff had more fun dancing with Sherry than he had expected. She was a good dancer and loved to jitterbug. The slow dances were great too as Sherry pressed her full body against Cliff crushing her big tits into his chest. He had an erection the entire time they danced close together and Sherry purposely pressed her thigh into his crotch. Cliff actually thought that he might cum in his pants at one point but he was relieved that he didn't. The dance was scheduled to end at 11:00 PM but Sherry told Cliff that she wanted to leave earlier. They left at 10:00 PM and Sherry directed Cliff to a parking area where they could neck.

Cliff had never been to that particular area for making out as he and Susan had always parked at another spot. This area was very secluded but there were already a number of cars with steamed up windows there. Cliff found a good spot and he turned off his car engine. Sherry was all over him and began kissing him driving her tongue into his mouth. Cliff's 1956 Chevy had a bench seat in the front so it was easy for them to maneuver. Cliff ran his hands up under Sherry's sweater and grabbed her big tits through her bra.

Sherry didn't protest when he unhooked her bra and fondled her naked breasts. Even though her tits were big they were firm and Cliff liked holding them in his hands. Her nipples hardened and they felt as stiff as the erasers on the end of his pencils. He twirled her nipples in his fingers and they seemed as long as the tip of his little finger. Cliff dropped one hand to Sherry's thighs and pulled her skirt up her legs. He ran his hand along the bare skin until he reached her panty covered pussy. He found her panties to be soaking wet and he slipped his finger under the elastic into her pussy. Sherry groaned into his mouth when he finger entered her and she mumbled something.

They broke their kiss and Cliff whispered, "What did you say?"

Sherry replied urgently, "Take my panties off!"

Cliff had never removed a girl's panty before as Susan had never let him. He took a hold of the waistband and pulled then down over Sherry's buttocks and off her hips. Sherry raised her body making it easier for him as he slipped them off of her. Cliff tossed the panties on the floor of the car and put his fingers back in Sherry's pussy. He finger fucked her pussy as she maneuvered her body so that his fingers were rubbing her g-spot.

"That's it keep you fingers there. Now rub my clit too. Oh yeah, like that, you got it," Sherry blurted out.

Cliff kept rubbing the hard flesh in her vagina with his fingers and her clit with his thumb. Sherry's body was out of control as she humped her hand racing toward her first orgasm. Susan had never behaved like this with Cliff and he was now totally caught up with Sherry's sexuality. Sherry moaned, groaned and humped her way to her climax and when it hit it rocked her body. Sherry grabbed Cliff head and pulled him to her as she yelled for him to hold her. With his free arm he wrapped it around her and buried his face in her tits. He began sucking on Sherry's nipple as he continued to finger her pussy.

Sherry lost it and her body gyrated frantically and Cliff held on as tightly as he could. His hand was drenched with her orgasmic juices and the smell of sex was rampant in his car. Sherry slowly recovered from her intense orgasm and as she did she kissed Cliff and thanked him.

"That was wonderful. Now it's your turn," she said as she reached for his belt buckle.

Cliff sat frozen to the car seat as Sherry unbuckled his belt and unzipped his fly. Next she pulled his pants down and the outline of his erection was prominent in his underwear. Sherry reached for his underwear and she pulled them down to his knees along with his pants. His erect 7" cock slapped against his belly and Sherry took it in her hand. It was another first for Cliff as he had never had his pants down in front of a girl. Anytime Susan had jerked him off he only had his fly unzipped. His cock stood out like a flag pole displaying his obvious desire. Cliff felt like he would cum any second as Sherry toyed with his dick. It was clear that Sherry was in complete control. Sherry pushed Cliff back against the car seat and then she knelt before him on the floorboard.

You have a nice cock and I am going to enjoy sucking it," Sherry said in a very sultry tone.

Cliff was speechless as he watched Sherry lower her head and engulf his cock in her warm sensuous mouth. He gasped as she closed her lips around it and then began to bob up and down. Sherry deep throated him and he felt her lips touch his pubic hair as she swallowed his entire cock. No one had ever sucked his cock before and he almost lost it at that moment. Sherry continued to suck his cock and she swirled her tongue around and nibbled the head driving Cliff crazy. Sherry sensed that he was close to blowing his load and she cupped his tight balls and massaged them as she tightened her mouth around his cock. That did it and Cliff could feel his cum travel from his balls through his scrotum as he started to cum.

"Oh shit, here it is. I'm cumming," he screamed but it was more of announcement than a warning.

Sherry stayed glued to his cock and swallowed every drop of his seed as it rushed into her mouth. Cliff came in droves and Sherry had to swallow quickly to keep his seed from running out of her mouth. Cliff could not believe how Sherry worked his cock and swallowed every drop. He had never expected a blow job much less have her swallow his cum. Sherry was pleased with his virile discharge and she knew that he would be hard again in no time so that he could fuck her. Cliff shot quite a load in her mouth.

Sherry sucked and nibbled and teased Cliff to no end. Finally he begged her to stop and he slid down onto the car seat to rest and recover. Sherry sat next to him and turned his face toward hers. She kissed him deeply plunging her tongue into his mouth allowing him to sample the after taste of cum. Cliff reached for her and took her in his arms. Cliff fondled her tits, thighs and ass as they kissed. He could feel himself getting erect again as they cuddled, petted and kissed. Sherry stroked Cliff's cock until he was hard again and then she moved to sit on him.

"I got so hot sucking your cock that I need to sit on your dick," Sherry gasped and quickly added, "I'm safe tonight to its okay to cum in me."

Cliff sat up and aimed his cock at Sherry's pussy. He slid in easily to the hilt and reveled in the warmth of her cunt. Cliff began to pump his cock in and out of Sherry's pussy as she bounced up and down on him. Sherry positioned herself so that her clit was in constant contact with his cock. Cliff began to pound Sherry's pussy and Sherry humped her hips back at him just as hard. The two of them fucked each other frantically breathing heavy and grunting and moaning. Sherry had another orgasm but continued to fuck Cliff toward his. Sherry lost count of her orgasms before Cliff finally filled her pussy with his seed. He was glad that she told him that she was safe because he would not have thought of it and he didn't have any rubbers with him.

Cliff stiffened and then thrust into her each time he felt his cum ejaculate. Sherry rocked with him and she clenched her cunt muscles squeezing every drop of cum from his cock. Sherry collapsed on his body as she felt the last surge of cum leave his cock. Sherry held him tight as he relaxed his body. Cliff had never felt so good in his life. He couldn't believe his good fortune in fucking Sherry. It had been an evening of firsts for him.

Sherry rolled off of him and sat next to him. Sherry then she kissed her way down his chest passed his stomach to his cock. Cliff gasped in surprise when Sherry took his cock in her mouth and sucked it clean of their combined juices. Then she moved up his body and kissed him deeply shoving her tongue in his mouth again. Sherry wanted to be sure that he got to taste both of them and that he shed any inhibitions that he previously had.

"That's enough for tonight. I need to get back to my aunt's house. Can we get together tomorrow?" Sherry asked.

"Yeah, I guess sure. What do you want to do?" Cliff replied tentatively.

"Meet me at my house tomorrow at noon. I'll tell my aunt that I'm going to the mall. Park your car a couple of blocks away and walk to my house," Sherry explained.

It was clear to Cliff that more sex would be on the agenda and he readily accepted Sherry's invitation. "Okay, I'll be there at noon."

Cliff and Sherry straightened up in the car while the defroster cleared the steamy windows. Cliff drove Sherry home to her aunt's house and they arrived just before midnight. Sherry kissed Cliff goodnight and reminded him about Saturday. Cliff drove home with the car windows open even though it was cold as his car reeked of sex. He didn't mind the smell but he didn't want it lingering overnight. It had been quite a night for Cliff getting his first blow job and losing his virginity. He felt great and he wondered what Sherry had in store for him the next day.


Cliff arrived at Sherry's house at noon on Saturday and he had parked his car several blocks away just as she had told him. When she answered the door Cliff was momentarily shocked as she was dressed in a bikini like outfit. Sherry ushered Cliff in the house and he followed her up the stairs to her bedroom. He stared at her big round shapely ass in the tight terrycloth bottoms as they ascended the stairs. He felt his loins stir and he was anxious to be naked with her in her bed.

Once they entered Sherry's room they immediately got undressed as Sherry directed. She pulled off her terrycloth bra top and pulled down her bottoms. She stood naked in front of Cliff and he admired her full figure. It was the first time he had ever seen a girl naked in person and his cock was throbbing. Sherry smiled at him and then spoke.

"Are you going to undress or what?"

Cliff snapped out of his stupor and quickly removed his clothes. His cock was stiff and sticking out from his body. "Well I can see that someone is happy to see me," Sherry teased and then she hopped in bed.

"Have you ever eaten pussy before?" she asked.

"No I haven't," Cliff confessed.

"Well I will teach you," Sherry told him.

Sherry lies back on her bed and spread her legs. Her hands went down to her pussy and she stroked her quim and opened it for Cliff to see. Cliff just stared at her in all her beauty lying on the bed. Her dirty-blonde hair spread across the bed, her big firm tits and hard nipples stuck up in the air and her voluptuous tanned body was splayed before him. Sherry held her arms open to him and then guided him to her body as he leaned in toward her.

Sherry coached him through every move of his first cunninglus experience. Cliff buried his tongue in Sherry's pussy shoving it in as if he was fucking her. Sherry directed the action and she soon had him nibbling on her clit while he fingered her pussy. Cliff was really getting into the action particularly because of the way he had Sherry squirming and tossing on the bed. Sherry moved her legs over Cliff's shoulders and pulled his head closer to her pussy. Cliff held on to Sherry shapely buttocks and squeezed and fondled her firm ass cheeks as he ate her pussy.

"Oh, oh, yes right there. You got it. Suck it; chew on it, that's the way to eat me, oh!" Sherry cried out.

Cliff continued to eat her pussy as he held her big ass tightly in his hands. He then moved his hands up to her tits and found her hard nipples. Cliff massaged her boobs and twirled her nipples in his fingertips as he continued to munch on her pussy and clit. Sherry was tossing and thrusting her pussy into Cliff's face and calling for him to eat her.

"Stick your finger in my ass," screamed Sherry.

Cliff had never fingered anyone's asshole and he was taken back by the demand. He snuck one hand behind Sherry's bottom and toyed with her asshole tickling the tight nether hole.

"Come on, wet your finger in my pussy and shove it in my ass," Sherry ordered.

Cliff stuck his middle finger in Sherry's pussy and got it good and wet with her juices. He then positioned it at Sherry's asshole and shoved it in. Sherry gasped with the abrupt anal penetration but soon had Cliff's finger buried in her ass. Cliff pumped his finger in and out of Sherry's ass as he continued to maul her pussy with his mouth. Cliff loved the feel of his finger in the warm recess of Sherry's ass.

Sherry stiffened and gasped aloud as she came on Cliff's face. Cliff held on to her with his finger still buried in her ass and his mouth glued to her cunt. He felt the waves of her orgasm rock Sherry's body and his face was flooded with her cunt juice. Sherry kept humping his face until the last of her orgasms passed and she flopped back on the bed.

Cliff slipped his finger from her ass and his hands found her breasts again. He stroked her tits and nipples as he gently licked her pussy dry of all her juices. Cliff finished eating her and then sat up kneeling between Sherry legs. Cliff followed Sherry's eyes to his cock.

Sherry smiled at him and said, "That was great. Now get that cock in my pussy and fuck me!"

Sherry again reminded him that she was still safe and that it was okay to cum in her. Sherry preferred that guys didn't use rubbers as she liked the feel of the warm cream shooting into her womb. Cliff leaned forward and aimed his cock at Sherry's pussy. He slid in easily to the hilt and reveled in the warmth of her cunt. Cliff began to pump his cock in and out of Sherry's pussy as she wrapped her fleshy legs around his back. Sherry pulled him in with her legs and positioned herself so that her clit was in constant contact with his cock. Cliff began to pound Sherry's pussy and Sherry humped her hips back at him just as hard. The two of them fucked each other frantically breathing heavy and grunting and moaning. Sherry had another orgasm but continued to fuck Cliff toward his. As she always did with boys, Sherry lost count of her orgasms before Cliff finally filled her pussy with his spunk.

Cliff stiffened and then thrust into her each time he felt his cum ejaculate. Sherry rocked with him and she clenched her cunt muscles squeezing every drop of cum from his cock. Cliff collapsed on her body as he felt the last surge of cum leave his cock. Sherry held him tight as he relaxed his body. Sherry rolled to her side and Cliff rolled with her. They held to each other and gently caressed each other's sweaty body. Cliff stayed hard after his initial ejaculation and Sherry noticed his state.

"I can see that you are ready for action again. Have you ever fucked a girl in the ass?" Sherry quizzed him.

"No I haven't. I really never thought about it," Cliff admitted.

"I love it in the ass. Will you fuck me in the ass?" Sherry asked sexily.

"I guess, if you want, yeah sure I'll do it," Cliff replied unsurely.

Sherry smiled at him and then got off the bed. She retrieved some lubricant from her nightstand and handed it to Cliff. Sherry then got on all fours and directed Cliff to lubricate her ass. Cliff got turned on by putting the lube in her asshole. He enjoyed fingering her hole and caressing her curvy ass. Sherry rotated her ass in arousal as Cliff inserted a second finger into her bung hole.

"Okay I'm ready for your cock Cliff, fuck me in the ass," ordered Sherry.

Cliff knelt behind her and eased his hard cock into her ass. He worked it in slowly and reveled in the methodical penetration of her luscious ass. Cliff had never felt anything like this before. Sherry's ass was a warm tight receptacle. Sherry used her sphincter muscles to perfection as she massaged Cliff's cock in her anal sheath. Cliff caressed both of Sherry's gorgeous ass cheeks as he fucked her ass deeply. They both sensed he was about to cum again and Cliff picked up his pace as Sherry squeezed his cock with more intensity.

"Cum in my ass, I want your cum in my ass," Sherry cried out.

Her words sent Cliff over the edge and he fired his second load into Sherry's hot ass. Sherry felt the warm sperm coat her rectal passage, a feeling that she never tired of. She squeezed her anal muscles and milked Cliff's cock dry of every drop of cum. Cliff continued to fuck her slowly until his cock softened and slipped from her ass. Cliff just looked at her beautiful ass and watched as trickles of cum ran out of her ass down her thighs and across the lips of her pussy.

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