Jason glanced at the clock and noticed that it was ten. He needed to get up soon but also felt like more sleep. He dozed a bit until he felt a hand touch his face. He opened his eyes to see a naked Kim leaning over him.
“Thanks, Jason,” Kim whispered.
“You’re welcome,” he replied softly as not to wake Claire. “I’m glad you enjoyed it.”
“Oh, I did. We’ll have to do this again if you’re willing,” Kim responded.
Jason almost jumped for joy but held back, willing himself. If they wanted to do it again, wild horses couldn’t keep him away. Oh, yes, he was willing alright. “Anytime.”
“Good. Would you care for a shower?” Kim asked.
“What about Claire?”
“She’s out like a light. She could sleep through a hurricane,” Kim stated.
“Okay,” Jason agreed, since he needed to get going anyway. It was now 10:30.
Kim backed off the bed and Jason cautiously followed. Kim was right, Claire never moved. Jason grabbed some shower towels along with his bath kit and Kim wrapped herself in the same blanket again. When they exited the room for the showers across the hall several brothers saw them and smiled, calling hello.
Jason got the water going as Kim hung the towels. They managed to make it behind a curtain and into a stall before anyone else entered. Jason loved Claire’s big tits but there was something incredibly sexy about Kim. It wasn’t like one thing stood out but the whole package together was like near perfection. He soaped her back for her eventually letting his hands move around front and cup her breasts. They were perfect handfuls for him.
“You have nice big hands,” Kim stated.
“Good for swimming,” Jason responded.
“Good for a lot of things,” Kim replied, turning to kiss him.
Jason eagerly kissed her back but wondered, ‘What am I doing here? I’m supposed to be with Claire, who’s in my bed now, and here I am with Kim.’
They soaped each other and washed each other’s hair. Kim’s long hair was far tougher to do than his. He loved her brunette hair and the way it shone brightly when wet and clean. Jason shaved and she watched but with both hands on his now stiff cock. When he finished rinsing he was ready to get out but Kim had other ideas.
Without saying a word, she squatted down and kissed his bulging cockhead. Her hands were already teasing the flesh and massaging his balls. Kim licked the head a few times before looking up.
“Can I suck it for a little while? I’ve wanted to since I first saw it last night,” she asked.
Looking down, Jason realized there was no way or no one in their right mind that would refuse her, “Sure you can.”
Kim smiled broadly and then surprised him by taking the complete head and more inside her mouth in one swift move. “Ungh,” he moaned as she proceeded to wash her tongue over and around his blood engorged cockhead. He could feel her tongue ring rolling across his flesh.
“Oh, my god, Kim. That feels great,” Jason praised.
Kim’s tongue teased back and forth under the head of his cock making him groan loudly as the silver stud ball rubbed deliciously across his sensitive nerve endings. She kept that up for a while until his legs started to shake, then she backed off.
“Like that?” Kim said with a knowing smile.
“God, that was fuckin’ great,” Jason growled.
He watched as Kim teased him for a while longer. He was content to cum in her mouth if that was what she wanted but again was surprised when she stopped and stood up. She kissed him. ‘Is she stopping?’ he wondered.
“What to fuck my ass?” Kim said, breaking the kiss.
“Huh … I guess so,” Jason concluded.
“I’d let you fuck my pussy again but I’m afraid I’m too sore. Your cock is big but I think I can handle it,” Kim proclaimed.
“You sure you can handle it,” Jason queried.
“It would help if we had some lube but saliva will have to do,” Kim said, spitting on the head of his cock and rubbing it in.
“You’re in luck,” Jason said, producing a little tube of Vaseline from his kit.
Kim gave him a funny questioning look but he just said, “Don’t ask.” She got it and chuckled.
Together they lathered her asshole and his dick. Kim leaned against the wall and Jason crouched to align his cock with her small little rear passage. Entry was even tighter than her cunt had been. Eventually the head popped past her sphincter muscle and lodged in her ass. Kim stiffened and grunted.
“Oh, fuck,” she said. “On second thought, my cunt couldn’t hurt this much.”
“You want me to … ”
“No, just give me a minute,” Kim professed.
Jason did then started pushing in slowly. It took a while but eventually he was deep in her bowel. She was unbelievably tight back there.
“God, you’re fuckin’ huge,” Kim lamented.
“Yeah,” Jason replied, smiling but she couldn’t see.
“Go slowly please.”
“Okay.”
He did, fucking her in slow short strokes. After a time he was able to build to a good rhythm. She was smaller than him and he had to keep his legs bent to fuck her ass. Kim braced herself against the wall and Jason palmed her nice breasts as he fucked her ass. When he started to feel that old familiar roiling in his balls, he picked up speed again and fingered her clit with one hand.
“Oh, fuck me,” Kim pleaded. “Your dick is so huge in my poor little ass.”
Jason fucked her harder. He was getting ready to blow and fingered Kim’s clit desperately in an attempt to get her there too. It was working and pretty much at the right time.
“Ungh,” Kim growled leaning back into him. “That feels so good. Fuck my ass, Jason. Cum in my ass.”
Jason sped up one last time but was rushing headlong to climaxing. He thrust into her a half dozen more times and then howled. He pushed one last time deep inside Kim and held still as his orgasm crested. His cum blasted into her ass and coated the abused walls of her tight bowel. Kim grunted and, leaning back into Jason, came too. His fingers were still teasing her sensitive clit and right nipple.
They rode out their respective climaxes together. If not for the shower they surely would have been sweating from the effort of the ass fucking. Kim slid off his beast of a cock and reached back to feel her gaping asshole.
“Wow, you stretched my poor little butt like a crater,” Kim said jokingly.
“You okay?” Jason asked.
“Yeah, sure. I will be. Thanks, Jason.”
“You’re welcome and thank you too,” Jason responded.
They cleaned each other off and went back to the room. Eventually they got Claire awake and up too. It was near noon so they grabbed a quick lunch together before the girls headed out. Jason got jealous eyes from most of the other brothers as they ate. The girls left but not before they discussed the next weekend and made tentative plans for Saturday again. Kim was fine with going out with Kyle again, who they ran into just before leaving and filled him in on the plans for next weekend.
Jason had to hurry. He had studying to do and then to get ready to meet Caitlin for golf. He called her to set the plans. He got Nina, her roommate first, and Nina went to get Caitlin. Soon Caitlin was on the phone.
“Hi, Jason,” Caitlin said.
Hi, Caitlin. Can you be ready by two?” Jason asked.
“Yes, but I have a question. You think Chad would like to go too with Nina?”
“Ah, I don’t know. He has a paper due tomorrow but he might be able to get away for a while. I could ask. It would be fun to double date. Is that what you two are thinking?”
“Yes, exactly. Nina had fun at the frat party and she would like to go play miniature golf as well,” Caitlin explained.
“Well, I’ll ask Chad but it’s fine with me if she comes with us whether he does or not,” Jason offered.
“Oh, that’s nice of you but I think she is hoping Chad can make it.”
“Hold on,” Jason said.
Chad was at his desk writing as Jason put the phone on mute. “Did you hear that?” Jason asked.
“Sort of,” Chad said. “Nina wants to go too and she wants to know if I want to double with you guys?”
“Exactly. Can you?”
“I’m almost done with this paper. Are you going to be back early?”
“I hope to be. I’ve been burning it at both ends and need to study and rest some before Monday is here,” Jason claimed.
“I’ll say you have. Well, as long as we are back relatively early I can go,” Chad stated.
“Good. You’ll make Nina happy and Caitlin also.”
Jason got back on the phone and told Caitlin. The girls were happy and the plans were set. At 1:45 Chad and Jason jumped in his car and headed for the girls dorm. Both were ready and by 2:05 they were on the road out of town to the one miniature golf course they knew to be open this late in the season.
It was a fun miniature golf course with some interesting yet tough holes. Jason won the competitive game in which the girls were surprisingly very good. In fact, Caitlin beat Chad but he beat Nina by just one stroke. The girls work at a miniature golf course must have helped their game. They had a great time with many laughs. Nina and Chad were good together again which gave Caitlin and Jason a few minutes alone at various times.
Caitlin shocked Jason about half way through the game. She snuck up to him when they were alone and said, “I’ve been thinking about something big since the last time we were together.”
“You have?” Jason questioned but with glee in his voice.
“Yes, I can’t seem to get him out of my dreams – wet dreams, I think you call them,” Caitlin said jokingly.
“Well, I know he was happy to make your acquaintance too,” Jason agreed merrily.
“Would he like a repeat performance?” Caitlin asked, smiling.
“I know we both would like that,” Jason replied.
“Good,” Caitlin said.
“What about Nina and Chad?” Jason queried.
“I think Nina likes him. That should take care of itself,” Caitlin hinted knowingly.
“I see,” Jason said, then, “Hey,” as Caitlin slapped his butt playfully.
After golf they went to get something to eat at the diner. It was just starting to get dark as they left. Caitlin suggested they go watch the planes again at the Mercer County Airport. No one seemed to care what they did as long as they didn’t just head back to the college.
Jason pulled the Camry to a stop in practically the same spot as before. Two other cars were there too but fifty feet away. Caitlin was up front with Jason and Chad in the back with Nina. Jason looked back and Nina and Chad were already in one corner of the backseat kissing. When he turned back to Caitlin, she was smiling and whispered to him.
“I told you it would take care of itself.”
“So you did,” Jason chuckled lightly.
Caitlin was already up on her knees leaning across the console. It was dark now but still plenty of light from the airport runway floods. The other cars probably couldn’t see what was going on as they couldn’t tell in those cars either. But inside the car, it was easy to see. She kissed Jason and tongues were immediately doing battle. Jason liked this woman’s forthright nature about sex. Caitlin seemed to know what she wanted and to go for it.
It wasn’t long before her hand was in Jason’s lap. He was already semi-hard from the hot kissing session and grew more so as Caitlin gently squeezed his clothed cock. Jason would have liked to be alone with Caitlin. He wasn’t much for group sex, at least with other guys present. The night before with Claire and Kim had been his first true threesome, but that was beautiful with the two women. In the car, he also wished they had more room. He knew Caitlin was a virgin and he was already on a roll, having popped three cherries already this weekend. Why not try for a fourth? He wondered what the record was for the contest in a weekend. ‘Four had to be up there,’ he thought.
Caitlin had been unbuttoning his shirt and kissing his neck and chest. She returned to his lips with a smile. They kissed again for many long hot minutes. His cock was now becoming uncomfortably tight in his jeans. Caitlin felt him shift and realized his discomfort.
“You need to let him out,” Caitlin said jokingly.
“It’s a bit cramped in there,” Jason chided.
“I bet based on how excited he feels,” Caitlin whispered giggling, returning her hand to his groin. “Shall I release the beast?”
Jason glanced back to see if Chad or Nina were looking but they were slumped down on the seat in the dark. Caitlin followed his eyes and from her position could see better. She looked for a second then turned back to him.
“They are quite busy,” Caitlin informed quietly. “Not likely they will care.”
“Okay,” Jason agreed.
Caitlin immediately went to work on his belt. Her expert hands had him open quickly and his dick free. Her fingertips teased the head making Jason moan softly. In seconds Caitlin could feel wetness on her fingers and realized he was leaking pre-cum. Her fingers smeared it around the head.
Caitlin looked into Jason’s eyes but without waiting for any kind of response leaned down. Jason could feel her hot breath blowing on his cockhead as her fingers worked both his cock and balls. He leaned back to give her more room. He would have liked to put the seat down but that wouldn’t work with the others in the back.
Jason next felt Caitlin’s mouth engulf the big head of his cock. He groaned as she swirled her tongue around the surface of his cockhead and applied suction and increased hand strokes to add to his enjoyment. He groaned again a bit too loud and knew the others had to hear. He couldn’t help himself though. Caitlin’s mouth was talented and knew how to tease him to the greatest affect.
“Oh, god,” Jason hissed as Caitlin descended lower.
He tried to be quiet but her mouth was feeling incredible on his cock. The combination of her hands and mouth were a lethal pair in bringing on his orgasm. He could already feel his nuts beginning to tighten for release.
Jason was just settling in to the blowjob and wishing he could see Caitlin’s tits and feel her pussy when a vehicle pulled up about ten feet away. He looked over to see an older woman looking at him. She turned from looking as soon as their eyes met but he wondered if she saw what Caitlin was doing. Caitlin’s head was below the side door but her ass was up in the air. It wouldn’t take much imagination to know what was going on if the woman had noticed. Jason immediately felt uncomfortable.
Jason ran his hair through Caitlin’s hair and managed to get her to look up. He nodded his head towards the door but Caitlin looked at him confused.
“Someone just pulled up right next to us,” Jason whispered.
Caitlin looked out the window, “They can’t see anything,” she said.
“You don’t think so? I know the woman saw me,” Jason claimed.
“You think they care?”
“I don’t know but it is just weird having an audience,” Jason professed.
“You want me to stop?” Caitlin queried.
“No, but … ”
“I got an idea. Want to go back to our dorm?”
“Yeah, sure but what about … ”
“Hey, Nina. Want to go back to the dorm?”
Jason thought he heard sucking and Chad moan just before Nina answered, “What? Why?”
“A car is right next to us. Not much privacy,” Caitlin stated.
Nina was now sitting up and Jason caught her face in the rearview mirror. Her lips were all moist. “Okay with me,” Nina said. “You want to head to our dorm?” Nina was heard asking Chad. He must have nodded yes, because she replied. “Okay, Chad says.”
Jason started the car and pulled away. Caitlin was still leaning over the console with her hands holding his erection. He glanced over at her as they drove down the road.
Caitlin smiled and said, “I’ll keep going if you promise not to hit anything.”
“I’ll be careful,” Jason said, smiling back.
Jason had trouble concentrating on the road with Caitlin lazily sucking his cock. She had him close to cumming twice on the trip to her dorm only to back him down. He was so horny he could have screamed by the time they arrived at the dorm parking lot. Fishing his cock back in his pants for the walk into the dorm would be difficult.
Caitlin leaned back to get out of the car like Chad and Nina were doing. She saw Nina glance over the seat, see Jason’s big cock, lick her lips, and then smile at her. Caitlin was smiling as she turned back to Jason and his worried look. He wasn’t moving.
“What’s the matter?” Caitlin asked, but then realized and giggled. “You can’t get him back undercover?”
“No … thanks to you,” Jason scolded but merrily.
Caitlin glanced around the full but quiet parking lot, “Lean back a little,” she said.
Jason did as he was told, moving the seat. Caitlin gave him an amused smile as she settled back into his lap. Her mouth was once again around his cockhead. Jason glanced around but they were fairly safe in the darkened parking lot. Caitlin was quickly playing beautiful blowjob music on his cock again. He groaned as she brought his desire back.
“Oh, fuck! You do that so well,” Jason grunted, getting closer to cumming.
Caitlin backed off only to say, “Thanks,” then was back on his cock.
Jason wanted more from this hot chick though. His thoughts turned to her pussy and he found himself wanting that cherry. ‘God, I’ve changed in the last few weeks,’ he realized. ‘Here I was accusing Mark of being immoral taking all those cherries. Now I’m the one that can’t wait to pop another.’
If Jason didn’t stop her soon he was going to explode in her mouth. He was so charged up he wanted nothing better but still he yearned for her pussy. He couldn’t believe he was doing it but he found himself pulling her off his cock just before his balls reached critical mass.
“What?” Caitlin questioned, sitting up and not sure why he had stopped her.
“Ahh … ,” Jason stuttered, not sure how to tell her all of a sudden what he wanted. That he wanted to fuck her. He finally got out, “What about you?”
“What, oh … I’m okay. I can get my kicks sucking you off,” Caitlin claimed.
“Well, I’d like to do something for you,” Jason stated.
Caitlin looked at him trying to read his face. Her hands were slowly stroking his saliva slick cock. She looked at him in such a curious way Jason wondered if he had asked too much. Finally, just as he was about to tell her forget it she responded.
“Chad and Nina are probably in our room by now. We could leave them alone and just climb in the back of the car.” Caitlin asked.
“Sounds good to me,” Jason agreed, unsure how they would have arranged things in the small dorm room anyway with Nina and Chad there.
Caitlin went first and Jason followed, staring at her ass as she went. Her weight loss program was paying dividends, he noticed. She didn’t have that much to lose in the first place and her efforts were emphasizing the curves of her nice body.
In the back seat they fell into each other’s arms kissing. The kissing grew hot and Jason’s exposed cock still jutted for his pants, erect and leaking pre-cum. Caitlin saw it and slurped on the head of his cock for a while. Jason was so aroused he couldn’t stand it anymore.
“God, Caitlin. I got to cum soon,” Jason pleaded.
“You want me to finish you and then we can work to get him hard again?”
“Sure,” Jason agreed, too far gone to care anymore.
Caitlin dropped her head back into his lap and half way down on his cock. Jason thought his head was going to explode as she began an aggressive attack on his dick. Her fingers teased his bloated balls and stroked his steely hard cock. Caitlin had three-quarters of his cock in her mouth and down her throat when he couldn’t hold back.
“Fuck,” Jason shouted.
Caitlin backed off his cock to the head just in time as Jason’s cum blew into her mouth. She had teased him so much he came in buckets much like the first time she had sucked him. Her mouth struggled to remain sealed around his cockhead and gather the significant cum as it filled her mouth. Just when she began to worry she couldn’t hold it all he slowed to a trickle. She sucked lightly on the head, gathering the last of his cum, before backing off and swallowing. Caitlin was glad to be able to breathe normally again.
“Oh, geez, Caitlin. That was awesome,” Jason groaned weakly.
“Wow, you cum a lot,” Caitlin chided. “I thought for a second there you were going to drown me.”
“Sorry … ,” Jason started to say.
“Just kidding. I loved it,” Caitlin added.
“Okay, good,” Jason replied.
“What now?” Caitlin asked.
“What? Oh, I ahh … I’d like to do something for you.”
Caitlin’s brown eyes search his face. Jason stared at the cute brunette. He really liked her. She had a great personality and cute dimples when she smiled. He believed she liked him too. He at least knew she liked sucking on his dick. They looked at each other for long minutes until Caitlin finally spoke.
“What’re you referring to?”
“Well … we could strip down and I could use my mouth on you like you just did to me. Or,” he couldn’t resist, “we could get it on.”
“Which would you prefer?” Caitlin asked, looking a bit unsure.
“That’s up to you,” Jason offered.
“What if I said both?” Caitlin asked.
“Really,” Jason queried.
“Yes, but … but I should tell you … ahhh, you probably won’t believe this but … ahhh, I’ve never done … either,” Caitlin finally got out.
“Ahh,” Jason tried to act surprised and was by the admission of no oral. “Would you like to?”
“Yes, definitely. But to be honest, Jason, I’m a little scared. I don’t want to mess things up between … ”
“That’s not going to happen,” Jason said. “Just let me help you.”
Jason started undoing Caitlin’s blouse. She watched him with rapt curiosity. Amazingly this blowjob artist had never given herself completely over to a man and she felt anxious but excited at the same time. Jason had her blouse open exposing the lacy bra beneath. Caitlin’s breasts were not as large as Claire’s or as shapely but they looked to be a full B-cup as Jason pushed her shirt from her shoulders.
Caitlin was leaning low against the backdoor to avoid being seen so she helped him by reaching behind and unfastening her bra. Jason watched the soft tantalizing flesh of her breasts come into view as he helped her take off the bra. He stared at her tits as her nipples were exposed. Caitlin had small brown nipples that were fully erect and still only less than a half inch long. Her nipples were cute in their tininess. Her breasts were decent handfuls and Jason’s hands immediately sought them out.
Caitlin looked into Jason eyes as if searching for any sign of rejection but instead found his returning smile. His hands palmed her firm yet soft tits and grazed over the bullet tight nipples.
Jason looked up from her tits into her eyes and said one word, “Beautiful.”
Caitlin seemed to exhale like she had been holding her breath and said, “Really?”
“Gorgeous,” Jason reiterated but differently.
“You’re not just …” Caitlin’s words and breath caught in her throat when Jason descended to her right nipple and sucked it into his warm, wet mouth quickly.
“Oh, god,” was all Caitlin could mutter then.
Jason feasted on each breast in turn and played with them for a good ten minutes. They were soaked with his saliva and slightly flushed from his constant handling when he undid her jeans. Caitlin helped him and soon they and her panties join the rest of her clothes on the floor of the car. She was naked before a man for the first time.
Jason pulled Caitlin to him making her sit lower in the car. As he did he got a good look at her pussy in the dim light from the few parking lot floods. She was not shaved like the other women had been this weekend. Maybe she didn’t believe in it or maybe she just hadn’t been prepared for them to go this far. Either way Jason found it refreshing to stare at her natural pussy.
Caitlin had a tuft of brown hair atop her cunt and more sparse hairs running down the sides of her labia. Her mounds were puffy and Jason could make out moistness in the slit of her pussy, evident as the light fell on her. He positioned himself between her open legs and glanced up to grin at the nervous looking Caitlin.
“I know you’re going to like this,” he said to ease her nervousness.
Caitlin watched intently as Jason settled over her sex and looked at it. His fingers parted the outer lips and opened her to his gaze. Despite her nervousness, she was wet inside and invitingly pink. Jason kissed the inside of her thighs and moved all around her pussy. He teased her a bit before actually moving to her inner core. Caitlin watched excitedly as he ran his tongue along her gash.
“Oh, geez,” Caitlin purred as she felt his tongue touch her.
Jason kissed Caitlin’s inner labia and then probed his tongue into her pussy. He sought out the entrance to her virgin cunt and wiggled his tongue around the opening. Caitlin moaned loudly as he pushed his tongue into her and tasted her growing wetness. He spent a good bit of time working on her cunt hole before moving higher.
Next Jason pulled back on her clit hood with his fingers and exposed her little knob. He teased all round it driving Caitlin crazy. Her fingers were now in his hair and she moaned as his tongue caressed the sensitive tissues around her clit. After teasing her briefly he swiped his tongue several times across her clit. Caitlin stiffened under him and grunted loudly. Jason could feel her increasing lubrication with his fingers and tongue. He tasted her nectar as it seeped from deep inside.
When Jason finally decided to suck her clit into his mouth, he had Caitlin built up to a frenzy. She grunted and started to buck up off the car seat to meet his probing tongue and sucking mouth. Jason could tell she was close. He moved two fingers to her cunt hole and teased around the opening but refrained from trying to penetrate her. The added stimulation along with his attack on her clit was too much for Caitlin.
“Oh, fuck! Jason … oh, god, I’m going to cum,” Caitlin screamed.
Jason hoped no one was near the car for surely they would have heard her. He tried to stay in place sucking her clit and finger teasing her as she squirmed and trembled. Her orgasm washed over her like nothing she had ever felt before. The waves of blissful pleasure emanating from her cunt spread like a raging fire throughout her body. Her own hands pulled and mauled her nipples as she shuddered to conclusion of her first oral induced climax.
Caitlin’s head was back and her eyes were closed as she panted and fought to recover from the wonderful orgasm. She felt Jason’s hands leave her but was not aware of much else. It wasn’t until she felt something new touching her cunt that she opened her eyes. Jason was positioned above her with his cock poised at her cavity entrance.
“You ready for this?” Jason asked, his lust-dominated voice showing his need too.
Caitlin would have liked a little more time to recuperate but could see that Jason was ready. ‘Oh, god, here it comes,’ she realized. ‘He’s going to fuck me now.’
“Caitlin, you ready or not so sure now,” Jason pressed, as he rubbed his cockhead along her slick pussy.
“You’re going to go slow, right?” Caitlin pleaded.
“Don’t worry,” Jason claimed.
She did worry though as she felt his cockhead nudge up against her opening. Jason pressed in until he was starting to enter. It didn’t take long for him to feel the obstruction blocking the entrance to her pussy. He aligned himself for the thrust which was becoming near commonplace for him this weekend.
“Ready?” Jason asked, as he leaned in to kiss Caitlin.
She kissed him back and replied weakly, “I guess so.”
Jason immediately thrust hard. He didn’t wait for her to prepare for the pain. He tried to catch her by surprise in order to get it over with before she could concentrate on worrying. He was becoming quite good at deflowering women and knowing just how hard to make the initial thrust. His cock pierced right through Caitlin’s hymen like a harpoon. He then held still giving her time to recover.
“Ouch …!” Caitlin cried. “Oh, shit. Ungh.”
“You okay?” Jason questioned.
“Shit! That hurt!
“Sorry but you knew it would at first.”
“Yeah … but it still hurts.”
Jason waited for her to relax. He could feel some of the tension leaving her as she settled back down as the pain weakened. He moved his cock just slightly allowing Caitlin to get used to it. She moaned a little but didn’t beg him to stop.
Jason thrust a little deeper which again made Caitlin moan loudly. She was incredibly tight and despite her moistness, it was slow going as her cunt reluctantly opened to accept the intruder.
“Oh, geez,” Caitlin groaned as his cock penetrated further. “You feel like a giant bat inside me.”
“It will feel better soon,” Jason tried to reassure.
“Shit, it feels like you’re stabbing a knife up into my belly,” Caitlin complained.
“Should I stop?” Jason asked.
“No, keep going,” Caitlin allowed.
Jason worked slowly but methodically and gave Caitlin all the time she needed to adjust to the pain and new sensations. Finally he started to develop a rhythm and in short order Caitlin’s moans started to sound more like pleasure than pain. Jason was thrusting deep into Caitlin with slow long strokes. Her hands clung to his sides trying to control his depth and speed. After a while though her hands were actually pulling him to her, so he sped up.
“Oh, geez,” Caitlin hissed. “That feels incredible now. Your cock is so huge inside me. I can’t believe how good it is starting to feel.”
“It’s going to get even better, babe,” Jason proclaimed.
“Oh, god! I think I’ll keep this thing inside me forever,” Caitlin shouted.
Jason, encouraged by Caitlin, was now fucking her at a strong steady pace. His balls were beginning to churn from the incredible tightness of her cunt. He wanted her to get off too and hoped he could hold out. Fortunately Caitlin was groaning loudly beneath him and he felt sure she was nearing her climax also.
“Ahh,” Caitlin moaned. “So good. That feels so good, Jason.”
“It’s going to feel better in a moment,” Jason claimed with a gasp.
He started fucking her harder, faster, and deeper. Caitlin groaned at the intense feelings running through her body. Her orgasm was coming on like a freight train. Exquisite licks of pleasure were coursing through her body, starting at her pussy, and manifesting themselves in her brain and nipples. Her fingers were aggressively tweaking them in an unending effort to answer the delicious itch there. Finally everything crested at once.
“Oh, fuck me!” Caitlin howled. “Oh, shit … Ahhh … ”
“Here’s my cum,” Jason shouted, realizing all at once they had given no thought to her unprotected womb.
“Ahhh … ” was all Caitlin replied as her orgasm took over.
Jason’s cock pumped load after load of cum deep inside Caitlin. She could feel his hot spunk mixing with her own juices and the combination only heightened her climax. Her body went stiff and her cunt clamped down on its own on Jason’s cock, milking him of every drop of cum he had left.
“God,” Caitlin finally muttered after her intense orgasm was over.
“Whew,” Jason added too. “That was great.”
“It sure was,” Caitlin agreed, letting the fact he had unloaded in her not matter for now.
They rested together until both were breathing normal. They then dressed and Jason walked her to the dorm. She offered for him to come inside but it was getting late and he had plenty to do, so he declined. They did agree to try to get together again the following weekend. Caitlin kissed Jason goodbye.
“Thanks,” she said. “That was great.”
“You’re welcome and thank you too,” Jason responded.
They kissed one last time and then Jason left. He wasn’t sure what happened to Chad and if he planned to stay the night or not. It was only a five minute walk across campus to the frat so he didn’t worry about waiting. Back in his room he tried to study but thoughts of the incredibly wild weekend kept entering his head. He wondered if he had indeed set a record for the most conquests in a weekend.
The next day after classes Jason went to work as normal. This time, however, he was on a mission to see if Kim was listed in Doctor Jenny’s records. He was delighted to find that she was. She had gone early on as a freshman to see the doctor. There next to her birthday date in the normal spot was the asterisk. Mark must have entered her card in the records as Jason hadn’t been working at the infirmary until second semester the previous year. So he now had the evidence he needed to prove four virgins undone in one weekend. Four cherrys popped over three days. Was it a record though? ‘Had to be,’ Jason thought. ‘No one else could possibly have done more.”
After work Jason raced back to the frat. He called Mark on his cell as he sprawled across his bed. Mark was working but about to head home too.
“Hey, Little Brother. What’s up?” Mark answered the phone.
“Hey, Mark. How’s it going, Big?”
“Stay in school. Work is definitely not as much fun,” Mark claimed.
“Oh, yeah? I guess I can see that, especially after this weekend,” Jason replied.
“Why? What was so special about this past weekend?
“What’s the record for most cherries in a weekend, three days?” Jason asked.
“Not sure I know, dude,” Mark said. “Why? You score a couple?”
“Better than that!” Jason confirmed.
“Yeah? Well, I did two on a weekend so you’re going to have to beat that. And I think if you look back in the log several brothers, you’ll find one dude that did three.
“How about four?” Jason boasted with pride.
“What? No fuckin’ way,” Mark said, but kept his voice low for the office.
“Yes, way, dude!” Jason exclaimed. “Four, count em, four from good old Doctor Jenny’s charts.”
“Wow! You’re the man. I knew you had it in you, that’s why I picked ya,” Mark stated.
“Well, that gives me five total. When did you hit five?”
“Not till at least Christmas as I recall so you are ahead of my pace. Good going, Little.”
“I might be on a record pace then,” Jason allowed.
“Might at that,” Mark said but chuckled. “Listen to you, the guy that wasn’t sure this was for him. Now you’re trying to break the record. Well, good luck.”
“Thanks.”
“Don’t forget to log your entries. You might forget details if you don’t. You might also call Mr. Caulfield. He is a generous guy and might be impressed with your weekend performance.”
“You think so?”
“Never know. He can surely appreciate what an unbelievable accomplishment four is in one weekend.”
“Í guess so.”
“See ya, Little. I got to finish up here. Call me anytime, especially with this kind of news. You just made my week,” Mark professed.
“Thanks, Big. Talk to you soon,” Jason responded.