Sherry Baby, Will You Cum Tonight

The two of them flopped down on her bed to rest briefly but Cliff would soon learn that they were just getting started. Sherry rolled onto her left side and Cliff snuggled up behind her. He draped his right arm over her and caressed her breast and tweaked her erect nipple. Cliff's cock was semi-hard and he pressed it against Sherry's hot ass. Cliff was curious as to when she started taking it in the ass so he asked her.

"When did you first start butt fucking?" he questioned.

"On the day after my 18th birthday a couple of months ago, you know Ziggi and Vinni, right," Sherry began.

"The Palmisano brothers, sure I play ball with them," Cliff replied.

"I had a birthday party at my house Friday night and Vinni and Ziggi were there with their dates. At the party they promised to take me out for my birthday on Saturday. We went to their house because their parents were away and we fucked all day. The first thing we did was with me on all fours sucking Vinni's cock and then Ziggi fucked me in the ass," Sherry described.

Cliff pictured Sherry on all fours with the two Italian studs banging her. He had seen Vinni and Ziggi naked in the locker room plenty of times and he knew that they were hung. Both Vinni and Ziggi had a reputation with the girls and it was known around school that they had their share of pussy. Cliff tried to imagine Ziggi stuffing his big Italian sausage in Sherry's virgin asshole.

"Christ, didn't that hurt?"

"Hell yes it hurt. Ziggi even greased me up good and it still hurt like hell. I couldn't do much about it as Vinni had my mouth stuffed with cock and he held me by the ears. Eventually the pain went away but I felt really bloated."

"Did he cum in your ass?"

"Yeah he did and it actually felt pretty good. The warm cream help soothe my ass." Then Vinni came in my mouth and I swallowed every drop as he held onto my ears. Next they switched places and Vinni fucked me in the ass while I sucked on Ziggi's cock. My pussy was on fire but they hadn't touched it yet, so I fingered myself until I came too."

"Wow that sounds so hot. I'm sorry that you felt pain," Cliff offered.

"They weren't done though and we had sex for nearly six hours. Once they goy hard again they double fucked me with Vinni in my pussy first and Ziggi in my ass. Then later they switched positions again. I kind of liked the double penetration because I had a cock in my pussy and I had many orgasms. By the time we were done they had cum four times each and I had two loads in my belly, two in my pussy and four in my ass."

"Unbelievable, how did you feel on Sunday?"

"I could hardly move and I felt really constipated. The following weekend I went out with the both of them again and they took me to their older cousin's house. Pauli has his own pad and the three of them triple fucked me until they had cum at least three times and I seemed to orgasm continuously. I had never had better sex and I was exhausted when they finally brought me home."

"Three guys at once."

"Yeah, one in my mouth, one in my ass and one in my pussy; then they rotated positions. It was pretty wild," Sherry sighed.

"I bet. Are you still seeing them?"

"No we got together a few times after that but then they moved on to other chicks. Hey, what's that poking me in the ass?" Sherry giggled.

Cliff realized that he was hard again and that his cock had slipped between Sherry's buttocks. He snuggled closer to Sherry and they kissed and fondled each other. Cliff kissed and sucked her breasts for a long time while his fingers played with her sweet pussy. Cliff next kissed his way down Sherry's lovely body and he soon had his face buried in her pussy. He brought Sherry to three moaning, writhing and gasping climaxes. He moved up beside Sherry and they kissed for a while. Finally, Sherry moved over him, slid down and took his turgid cock in her hand and began to stroke it. Smiling, she slipped her lips over its velvet head and slid it into her mouth. Sherry licked it then she moved her mouth up and down. Her mouth moved up and down his shaft and she rolled his large testicles in her hands.

Sherry continued sucking his cock for several minutes till it was stiff, rigid and menacing looking and she had Cliff moaning. She pulled back and got on all fours, shifting her hips so that Cliff had to mount her from behind. Cliff moved behind her and pressed his wet gleaming organ against her pussy. Sherry reached back and guided him into her. Slowly he thrust forward, his cock slipping deeper with each stroke. He pulled back each time letting her pussy juices grease the way.

"Oh God, that feels good. Deeper, fuck me, deeper. Oh yes!" Sherry moaned aloud. "Oh, I love your cock."

"Oh, Cliff, that feels so wonderful. I'm so glad we got together. Your cock fills my pussy so well. Fuck me slowly." Sherry begged.

Cliff held her by her hips and with long slow strokes fucked her. They fucked for what must have been five minutes till Sherry began to moan.

"Oh, Cliff, fuck me faster. It feels so good, fuck me hard. I love it when you fuck me hard and fast. Fuck me hard. Yes, like that," Sherry begged.

Cliff was more than eager to comply, and his muscles rippled as he began to stroke long and hard against Sherry's body. His hips slapped against hers causing Sherry's lovely breasts bob and swing as he slammed into her.

"Oh yes, Cliff, that's the spot. Fuck me hard right there. It feels so good. Yes, like that. That hits the spot that feels so good. Fuck me hard, harder!" Sherry cried out.

Cliff bent over and with his hips still thrusting he slipped one hand down to finger Sherry's clit, the other reached under and caught one jiggling breast. His hips moved faster slapping against her body. She moaned and sobbed her passion. She cried out and threw back her head as she climaxed.

Cliff continued to thrust. He quickly brought her to another climax. After her third climax, Cliff joined Sherry in a fourth as he pulled out of her pussy and shoved his cock back up her ass. Sherry loved the feel of warm seed flooding her ass and she cried out telling him to cum in her ass. Cliff and Sherry separated and lay together kissing. They talked for a while and then Sherry took his cock in her mouth and licked his and her juices off of it, cleaning it. She began to suck it in and out, and in a few minutes he was hard again. Cliff was still amazed that Sherry would suck a cock that had just been in her ass.

"Now I want your big cock in my ass again. I want you to fuck my ass again and cum in my asshole again," Sherry said in a sultry tone.

As Sherry moved to all fours she placed her head on the bed and turned her face to one side as she arched her back and accentuated her big curvy ass. Cliff pushed a thick finger into her asshole and then he added a second finger which caused Sherry to gasp. He worked the two fingers in and out of her ass stretching her as much as he could. Cliff then placed his impressive erect cock between Sherry's beautiful smooth round ass cheeks and pushed into her asshole.

This time Sherry moved away from him and ended up on the bed lying flat on her stomach. Cliff followed her to the prone position and lay on top of her shapely body with his cock between her ass cheeks and in her asshole. Cliff began to hump Sherry at a slow pace and then faster with his hips pumping into her. Sherry's screams and moans were louder than ever as her body took Cliff's 7" cock. Cliff lifted her back to her knees on all fours and reached around to feel her tits. Her nipples were rock hard as he twirled them in his fingers. Cliff then moved one hand down to play with her pussy and Sherry went wild humping her hips faster and faster. Cliff then placed both hands on her hips and watched his cock penetrate her curvy ass as he moved her hips in time with his humps.

Sherry yelled for the world to hear, "Oh my God, fuck me, fuck me, please fuck me!"

Cliff complied with her demands and pounded her ass as hard as he could. Sherry squeezed her ass cheeks together and she orgasmed as Cliff joined her and shot another huge load of cum deep into her ass. Sherry screamed and moaned as she felt Cliff pump several shots of cum into her rectum. Sherry's beautiful body radiated heat as Cliff pumped cum into her ass. Sherry was almost out of breath but started to return to normal breathing as Cliff caressed her body lovingly. Cliff eased his cock from her ass and traces of cum ran out of her asshole between her ass cheeks, over her pussy and down her inner thighs. Sherry scooped cum up with her fingers and licked them clean. Cliff flopped on the bed next to her and Sherry once again dropped down and took his softening cock in her mouth and sucked it dry.

It took quite awhile but Sherry got Cliff hard again. Cliff moved to his back and Sherry straddled him and reaching down she guided his swollen cock into her pussy, slipping down till she had all of him in her. She leaned forward, kissed him and then she began to rock up and down on his hard cock. Sherry reached back fondled his swollen scrotum and rolled his testicles around. Sherry's lovely big firm breasts bounced and the Cliff could see her nipples erect and pointed. Cliff fondled her tits as Sherry moved up and down, her hips thrust forward as she moved on him.

Sherry rose and fell as she rode Cliff's hard organ. He caught her hard long nipples in his strong fingers and pulled on them gently. He stretched them and wiggled her breasts from side to side using her nipples. Sherry moaned aloud. She rode him for a long time before she climaxed. Sherry collapsed on Cliff's body and then he rolled her to the side. Cliff didn't cum again and he was sure that he wouldn't be able to that day. However as they lay in the spoon position, Cliff slipped his cock back into Sherry's ass. They fucked in this position until his cock softened and slipped from her asshole.

"You can really cum a lot," Sherry whispered.

"I think that you had something to do with that," Cliff replied although he knew that his ejaculations were always volcanic like and that he could cum at least four times a day. However that day was the first time he came four times with a girl.

They rested awhile and then Sherry suggested they shower and get dressed. She straightened up her room and stripped the bed. She knew that she would have to wash the sheets and then remake the bed. Cliff finished his shower and got dressed. Sherry was still naked when he left the house and he could not resist grabbing her ass as he left. He walked the several blocks back to his car and then drove home. It had been quite a day for Cliff and he was exhausted and hungry.

As he drove home her thought about everything that he and Sherry had done. He had fucked her pussy and ass; she had sucked his cock and he had eaten her pussy. Those things were all firsts for him. He had been worried about not losing his virginity but that worry was over. He had never expected to learn so much so fast. He wondered if he would go out with Sherry again and how he would deal with Susan if she wanted to get back together. Cliff went home made himself something to eat and then crashed in the TV room contemplating his remaining days at high school.

EPILOGUE

The following week all hell broke loose as it was all over the school that he and Sherry and made it together. Susan was livid and vowed never to speak to him again. On the other hand Vinni and Ziggi slapped him on the back and congratulated him for busting his cherry. A couple of girls who were known action at school approached him. They said that Sherry said that he was a good lover and they asked him if he wanted to go out sometime. Cliff smiled and told them he would think about it.

As it turned out Cliff did date some of the other fast girls and he had great sex with them. He also dated Sherry a few more times and had incredible sex with her. By the time he graduated he was having sex several times a week with different girls and he loved his new found life. After graduation, Cliff enlisted in the Marine Corps as planned and he felt very confident bout his sexuality as he headed off to boot camp.

It would be over four months before Cliff got laid again but he experience came in handy for his first duty station. Cliff was assigned to security guard duty in Naples, Italy. It was a two year duty assignment and he had a marvelous time in Italy and other countries he visited, particularly France. He would learn that many French women loved anal sex and he was only too glad to accommodate them.