He waved back to Stephanie and then drove away. He had a lot to do before the party including a shower. He had time but would have to rush to be done before the women started to arrive. Jason grabbed a fast dinner at the frat, got showered, dressed, and prepared his room with Chad for the night’s activities. Kyle stopped by and pitched in too. He wanted to make sure everything was still on with Kim and Claire.
Jason wasn’t sure exactly whom he wanted to see more: Claire or Caitlin. Actually he knew it was another double with Kim and Claire he really wanted, but that might not happen. He was not surprised though when Caitlin and Nina showed first just as the party was starting. Jason had managed, this time, to get out of working the party but Kyle and Chad both had to take turns serving beer and punch to the guests. The main purpose after all was to attract pledges and each brother had to do their part to add to that. Jason was just lucky to have worked the last party and therefore had time off this time.
Kyle took over the beer tap from Chad, as planned, when Caitlin and Nina arrived first. The guys had planned this out so as to maximize time with the ladies. Jason and Chad talked with Caitlin and Nina at one of the tables until the party really got going. One of the brothers was acting as a DJ and they started to dance. Nina was really into Chad after they had spent the night together. They were dancing a real bump and grind, Jason noticed.
Jason was having a good time with Caitlin when he happened to look over by the bar and saw Claire staring at him. Kim was talking with Kyle as he handed her a beer. The look that Claire gave Jason was one of disapproval of his close dancing with Caitlin. Immediately, Jason realized his plan to have them both here together was flawed. Neither one of them would want to play second fiddle to the other and keeping both happy would be a full time job. His expression must have shown the change in his mood.
“What’s the matter?” Caitlin asked, but her gaze had followed his and she knew.
“Nothing,” Jason said, but not with much sincerity.
“You know her?” Caitlin asked, nodding her head towards Claire and the bar.
“Yes,” Jason confessed.
“Looks like she wants you over there and not with me,” Caitlin claimed and she had to practically shout it over the music to the point Chad and Nina might have heard.
“I should say hello. Do you mind?” Jason asked, but immediately realized he was wrong either way.
“You want to come?” he added, thinking that might help somehow.”
“Okay,” was all Caitlin replied stiffly.
The dance had just ended so Caitlin followed Jason to the bar. She felt awkward trailing Jason through the crowd and didn’t really want to meet her obvious competition.
“Hi, Claire,” Jason said as they approached.
“Hi, Jason,” Claire responded.
“Claire, this is Caitlin. Caitlin, Claire,” Jason tried to say cheerfully like they should be glad to meet.
“Hi,” Caitlin said and Claire nodded hi back.
“How long have you been here?” Jason asked, trying to think of something pleasant.
“Long enough … about ten minutes,” Claire answered.
This was indeed awkward and the conversation was difficult, with Jason forcing responses and peppering the women with meaningless questions to keep it going. To make matters even worse, as if that was possible, Kyle was being relieved from bar duty and hauled Kim off to dance. If Jason left to dance again with Caitlin or Claire, it would leave the other alone at the bar. And, as if that wasn’t bad enough, he turned to Caitlin and she was watching Chad leave with Nina down the hall to the stairs.
‘Fuck,’ Jason thought. ‘I’m screwed with this situation. What the hell was I thinking and now what the hell am I going to do?’
The only thing that came to him was to invite them both to his room for a stiffer drink. He could sure use one himself right then. The only problem with that plan might be Nina and Chad already being in the middle of something there.
“You guys want to go to my room for something else to drink?” Jason suggested.
Caitlin exchanged glances with Claire but agreed. Jason then turned to Claire and she nodded okay too. They walked to Jason’s room through the crowd, with Claire leading and Caitlin trying to stay by his side rather than trail. As they walked he spotted a cute redhead standing talking to another brother in the hallway. He thought he remembered her name as Beth. They had struck up a conversation at the infirmary and as he recalled she was a swimmer like him, a virgin too. As he walked past, the redhead looked right at him and smiled as if she recognized him also. ‘Geez, what a day,’ Jason thought.
They got to his room and Claire immediately sat on the bed. It was almost like a signal to Caitlin, ‘this is my domain.’ Caitlin took the desk chair. Jason was relieved that apparently Chad and Nina had gone somewhere else. He asked each what they would like but they left it to him. He made them a blender of margaritas. For everyone, the first drink went down quickly, while the conversation was at best cordial. The second blender of drinks saw the women soften up and begin to talk to each other, even laughing at the awkwardness of the situation.
Jason had just made the third blender of margaritas when Chad and Nina entered the room. They looked and acted stoned. They had probably been invited to another room to smoke. Jason poured two more glasses for them. His immediate fears of Nina and Caitlin ganging up on Claire soon faded as the conversation proceeded nicely. It had become more like a little party and everyone appeared to be having a good time. He even caught Claire and Caitlin looking at each other with more than passing interest. Jason already knew that Claire was not opposed to girl on girl.
With the fourth blender of margaritas, Jason ran out of mix and also low on tequila. He had not planned for this kind of party but was pleased it was going well. Nina seemed to be getting along fine with Claire, as Caitlin was too. The two freshman girls were asking Claire her opinion on several different topics. The drinks had more than loosened everyone up and Claire seemed to show interest in Nina too.
The knock on the door was answered by Chad. Kim and Kyle came in looking a little disheveled and equally lit from the beer or other booze. They joined the party and things really became wild fun. Sexual tensions were high and the room seemed ready to bust out in an orgy. The floor and beds were basically strewn with bodies. Nina kissed Chad at one point, which soon led to Kim and Kyle making out. Even Jason found himself sandwiched between Caitlin and Claire. He alternated kisses between them. Both women had their hands in his crotch, which quickly became hard packed in his pants.
Jason’s hands began working up under the shirts of each girl and had moved their bras aside to palm their breasts. Claire and Caitlin moaned as he toyed with their nipples. Their hands had freed his cock from its confines and were teasing it to rock hardness. They continued to kiss each other. At momentary pauses, Jason noticed the girls eying each other and not in a bad way.
“Whose tits you like more?” Claire asked, with a mischievous smile.
“Mine?” Caitlin said, but more as a question than answer.
“Check out these,” Claire said, more to Caitlin than Jason, and pulling off her shirt and bra in one over the head move.
“Wow, those are beautiful,” Caitlin admitted. “But look at these,” removing her top too.
“Nice! Well, Jason…?” Claire said. “Whose are nicer?”
“I have to pee,” Jason said, knowing he couldn’t possibly answer this question.
Caitlin’s were nice, full and firm, but Claire had the tits of a goddess, so though they were both great, Claire’s won hands down.
Soon Kim and Kyle disappeared again, probably to his room. Chad and Nina had climbed into the upper bunk and were under the covers. The bed started to creak from their hidden movements. Jason still needed to piss and left briefly to do so. When he returned, he found Claire and Caitlin naked and kissing in his bed.
“I see you two are having fun,” Jason stated.
“Waiting for you,’ Claire claimed.
“Yes, come here,” Caitlin exclaimed.
Jason stripped and climbed between them on the bed. The girls’ hands immediately grabbed his big soft cock. Caitlin massaged his balls as Claire stroked his shaft. He had hoped to get with Kim and Claire again but this was possibly even better. His cock became rock hard in seconds. Claire kissed the head of it and pointed it towards Caitlin to do the same. She did and Jason moaned deeply. This was getting more erotic by the moment. Having two women sucking on his cock at once was a fantasy of Jason’s.
Claire massaged Jason’s balls as she watched Caitlin kiss and then suck on the head of Jason’s dick. Claire kissed Jason with an active tongue. It was a very hot kiss and both groaned into each other’s mouth. Caitlin continued to suck on Jason’s cock,
“You like kissing me while she sucks your dick?” Claire asked wickedly.
“Yes,” Jason managed to say.
Claire’s hand started stroking the part of Jason’s dick not in Caitlin’s mouth. Jason and she kissed passionately again. Jason realized if this kept up he would surely cum soon. Claire left the kiss and moved down to suck on Jason’s balls. After a couple minutes of that, Caitlin offered her his cock. Claire took it and went deep as Caitlin now kissed him and played with his balls. They were starting to churn with pent up pressure.
“Oh, god! I’m going to cum soon,” Jason growled.
“She give good head?” Caitlin asked.
“You both do,” Jason said, trying to remain diplomatic.
Claire stopped and looked up. “Kiss the other side, Caitlin,” Claire said.
Together the girls ran their lips up and down Jason’s cock. Pre-cum boiled from his hole like lava from an agitated volcano. They took turns licking it up and teasing his cockhead with their tongues. At various points their tongues flicked against each other. Jason watched this totally erotic scene and nearly came at that instant.
The bed was still shaking, this whole time, from the obvious fucking going on above. It wasn’t just the swaying and creaking of the bed, but the groans and words of encouragement from Nina that told the whole story. Jason tried to focus on other things, to prolong his orgasm from the delicious sensations the two girls were giving his cock. He tried hard to think about other things, but it was difficult with Nina saying, “Oh, god, Chad. I’m going to cum again. Keep fucking me … harder … harder.”
Jason looked back down at the two attractive women sharing his big cock and kissing each other occasionally. Claire and Caitlin had obviously found they were attracted to each other more than any thoughts of jealousy. Jason moaned loudly as one sucked his cockhead and the other tongued his shaft and licked his balls.
“Oh, shit! I’m going to cum,” he shouted.
As he did, he heard Nina scream, “Oh, I’m there! I’m cumming!”
The girls stopped sucking on Jason’s cock just before he exploded. They giggled to each other as they too listened to the noises from the bed above.
“Sounds like Nina’s having a good time,” Claire said jokingly.
“Sure does. What do you say one of us ride this big dick,” Caitlin offered.
“Definitely! You go first,” Claire allowed.
Claire pushed Jason back down flat on the bed as Caitlin swung into position and mounted him. She was wet but her pussy was still as tight as a velvet keyhole. She eased down on him as Claire kissed Jason. He spread her cunt deliciously as she settled onto him slowly. Caitlin had missed the feeling of being completely stuffed with cock.
“Oh, god. You feel so good inside me, Jason,” Caitlin moaned.
“Go slow, Caitlin. He looks like he might cum any second,” Claire mused.
Her beautiful left tit was over his mouth making it difficult for him to answer. His hand kneaded the other one as Claire fed them to him. She was right. Jason’s balls were aching for release. If Caitlin hadn’t been moving as teasingly slow as she was, mostly just grinder her pussy on his cock, he would have cum instantly. Instead, Caitlin was able to elevate her own desire while holding his just simmering below the surface.
“Oh, geez,” Jason growled when Claire pulled her nipple from his mouth.
“You better take it slow, Caitlin,” Claire warned with a mischievous smile.
“I am,” Caitlin gasped as her climax neared.
Jason watched as Claire swung her leg over his head. Her nearly bald pussy spread for him to see. Her dewy wetness was evident as she settled over his head. It didn’t take a genius to figure out what Claire intended. He watched her pussy descend to his mouth. Seconds later his vision was obscured by the closeness of Claire’s ass cheeks to his face. His tongue leapt out to taste her sweet pussy as she pressed it to his face.
Jason couldn’t see but he could hear Caitlin moaning. He assumed it was from his cock deep inside her, stretching her wide, but he didn’t also realize Claire was sucking the freshman girl’s tits and fingering her clit. Caitlin started riding his cock harder. Jason tried to concentrate on sucking Claire’s cunt, but the tightness of Caitlin’s near virgin snatch milked his cock like practiced farmer’s hands.
He grunted into Claire’s cunt as he felt Caitlin’s pussy spasm on his cock. Her muscles clamped down even harder and he lost it too. A flood of pent up cum blasted into Caitlin’s quaking pussy, adding to her already blissful orgasm. Jason wasn’t sure if he was going to finish getting off before he passed out from lack of air. Claire’s pussy was pressed so hard to his mouth, he could barely breath. He was nearly caught by surprise when she too trembled and flooded his mouth with her juices. He pushed her up a little with his hands to breathe and not to drown as he tried to drink her abundant fluids.
Eventually, Claire rolled off Jason to the side and Caitlin collapsed on top of him. The room was filled with the sounds of their heavy breathing. After a while, Jason opened his eyes. He could feel Claire’s wetness all over his face. He watched Caitlin open her eyes as well. She smiled at him with those cute dimples. Then she surprised him by licking Claire’s juices off his lips, cheeks, and chin.
When Caitlin had cleaned his face, she also stuck a tit in his mouth. As he took hold of the nipple between his lips, he felt the bed move, then hands on his limp, wet cock. Next he felt a mouth enclose over the head and take most of him in.
Claire’s expert mouth worked on his soft cock gently. She started with practically the whole thing in her mouth. After a little while, she managed to get it to stiffen again. Meanwhile, Jason was sucking Caitlin’s tits and kissing her passionately. Claire’s hands massaged his balls, adding to his increasing arousal. Caitlin swung off of Jason’s chest to help Claire blow him. When she dismounted, she left a puddle from her cunt of his own cum and her fluids on his upper abdomen where she had been resting.
Jason pulled a pillow behind his head so he could watch the two cute women suck and lick his shaft. They took turns sucking on the head and fondling his loose hanging balls. Since he had just cum his ball sack was relaxed and his testicles hung down between his ass cheeks. Caitlin went after them and sucked each nut, in turn, into her soft, wet mouth. Jason moaned appreciatively as they teased him and enjoyed the many wonderful sensations coursing through his body from the girl’s actions to his genitals.
When Jason was fully stimulated, Claire took her turn astride his cock. She was fully aroused and anxious to fuck his cock. Her cunt was as tight as Caitlin’s and she had to settle on the big dick slowly also. She pressed down hard, at intervals, until Jason was fully embedded in her cunt.
“Oh, geez,” Claire gasped. “That feels wonderful taking that big monster inside me.”
“You feel great too,” Jason stated.
“It’s hot watching you two fuck,” Caitlin said.
Caitlin lay beside Jason as Claire rode up and down on his big dick. She alternated between watching, kissing Jason, and sitting up to play with Claire’s magnificent bouncing tits. Claire was soon into a full ride and moaning loudly from the delicious contact. Jason’s hands guided her hips as she bucked on top on him.
Claire had two orgasms before Jason started to feel his own need to cum approaching. He began to fuck up more and more into her tight wet pussy. Caitlin stimulated Claire’s clit with her hand like Claire had done for her. The deep penetration of Jason’s cock and Caitlin’s fingers on her clit soon had Claire cumming again.
Claire slowed a bit after she came, which kept Jason from peaking. He ground his cock into her, making her moan with pleasure. Claire surprised them both by climbing off and giving Caitlin another turn. Caitlin eagerly took her place being horny again from watching the two of them fuck. Caitlin rode Jason slowly, keeping him from cumming.
Once again Claire shifted over top of Jason, aligning her cunt with his mouth. He ate her out as she sucked on Caitlin’s nipples. Both girls had their hands all over the other’s tits as Caitlin picked up the pace riding his cock. Claire’s fingers once again teased Caitlin’s clit, which caused her to peak quickly. The added stimulation of Caitlin bouncing feverishly on his cock pushed Jason to the point of no return. He tried to still eat Claire’s pussy as he felt his climax coming on.
Caitlin came first, shouting out her pleasure. Jason next, followed closely by Claire. The bed shook from the three bodies trembling and quaking. Each groaned loudly as they came.
“Oh, fuck!” Caitlin yelled. “Ahh … that magnificent cock … ”
“Eat me, Jason. Keep going,” Claire pleaded, her fingers still teasing Caitlin.
“Ungh … ” was all Jason could muster, as the tightness of Caitlin’s cunt milked the pent up cum from his balls.
He hosed her insides with his cum for the second time that night. They stayed like that for many moments until everyone was spent. They collapsed in a ball on the bed. Somehow they managed to all get under the covers with Jason in the middle. They slept like that, sandwiched into the tiny bed.
Jason woke the next morning to the delightful feelings of someone playing with his cock. He looked down to see them both smiling back on either side of him. He was already hard but also in need of the bathroom. He suggested a shower together and the girls agreed without a second’s thought.
In the shower, things got even hotter. It turned Jason on immensely to watch Caitlin and Claire kissing and soaping each other up. They spent nearly as much time playing together as with him. He fucked them both in the shower. First he fucked Claire, then Caitlin. He managed to make them both cum. When it was his turn, Claire pulled him out of Caitlin and went down on him. She sucked up all his cum as he ejaculated in her voracious mouth. He then watched as Claire smiled at him and devilishly shared her cum prize with Caitlin. The two women squealed with delight as they battled with tongues for the last taste. Jason knew this might not be the last time either.
Nina had spent the night with Chad too but they were both gone when the threesome got up. Kim must have spent the night with Kyle as they never saw those guys again either. Caitlin and Claire left after they grabbed some breakfast together. Once again, Jason got jealous looks from his frat brothers as he obviously ate with the two girls he had slept with after the party.
Jason was three hours into studying when his cell rang. He could tell from the caller ID it was Stephanie but not sure how she got his number. He only had hers, he thought.
“Hi, Stephanie,” Jason answered.
“Hi, Jason. I hope I’m not catching you at a bad time?”
“No, just studying.”
“How was your party last night?”
“Great.”
“I almost came by but figured you would have asked me if you wanted me there.”
“You could have come but I might not have been able to spend any time with you. How did you get my cell phone number anyway?” Jason probed.
“I’m sorry. I saw it sticking out of your pants pocket when you were swimming. I’m good with numbers and I guess I memorized it,” Stephanie said.
“So you must have had a date then at the party?” Stephanie continued.
“Yes,” Jason stated, but didn’t tell her there were two.
“I see,” Stephanie responded.
“Stephanie, is everything alright? I mean if I didn’t know better I’d say you were stalking me or something.”
“Oh, I’m sorry. I just wanted to talk to you again. Actually, I was hoping to see you later if you’re available?” Stephanie asked.
“What about?”
“It’s kinda personal. I was hoping to talk to you about it.”
“Well … I suppose I could use a study break. My eyes are getting weary looking at these pages. Want to join me for a run?” Jason asked.
“A run,” Stephanie said as someone not used to that suggestion.
“Yeah. We could meet on the quad and go for a jog out back. I know a good trail.”
“Okay, but I have to warn you, I haven’t run since high school. I’m going to be a bit rusty,” Stephanie confessed.
“Do you run as good as you can swim?” Jason asked.
“Yeah … I’d say so,” Stephanie claimed.
“Well, we should be okay then. See you in twenty minutes?”
“Okay,” Stephanie agreed.
Twenty minutes later they met on the quad and started out. Jason kept the pace slow and Stephanie did well for the first half mile. When they crossed the old freight railcar lines at the back of the campus, before entering the wooded path, Jason could tell she was faltering. He had to admit, though, she looked good in her running outfit, which hid nicely the extra pounds.
They could only talk a little as they ran. Jason could talk near normally but Stephanie was now huffing and puffing. She was finding it difficult to stay with him. They had only made small talk to this point, so it was obvious to Jason that she wanted to wait until she could talk more relaxed.
“There is a clearing a half mile ahead on this trail. Why don’t you head there and I’ll run ahead and meet you there,” Jason said.
“Sounds good to me,” Stephanie said, looking for any reason to stop.
“Okay … see you there,” Jason said and he was off in a hurry.
Stephanie stopped running instantly and watched as Jason ran up the trail faster than they had been going and out of sight. She quickly caught her breath and walked the half mile to the clearing, which she found easily. She was about to wonder where he was when she spotted him on the other side waving. She started walking towards him as he did too. They met in the middle. He took her hand and pulled her to a spot where there was a large depression in the field, ten feet around, and two feet deep. Once in it and lying down, someone would have to nearly stumble upon them to see them.
“What now?” Stephanie asked.
“We sit but wait a minute.”
Jason lay down in the foot tall dry grass. He spread his arms and legs as if he was making a snow angel. The grass bent and formed a nearly round flattened circle. Then he sat up and beckoned Stephanie to sit down in one part of the open circle across from him.
“Neat … good idea, Jason,” Stephanie praised him.
“My girlfriend and I used to come here,” Jason offered. “It was her idea.”
“Used to come here?” Stephanie queried.
“Yeah, that was last year and before she broke my heart. I don’t see her anymore.”
“Oh … so you’re not seeing anyone now?”
“Well, I didn’t say that. I’m seeing a few women, but nothing serious anyway right now,” Jason allowed.
“It must be nice to meet people so easily. I’m not good at that at all,” Stephanie claimed.
“What do you mean? We just met didn’t we?” Jason said.
“Yes, but that was mostly your doing, for which I am grateful by the way.”
“Oh, it was nothing but friendly conversation,” Jason proclaimed.
“Well, thanks anyway. You’re the only person besides my roommate that I even talk to on campus.”
“No other dorm friends?” Jason asked.
“No, none. I guess I’m a bit of a loner,” Stephanie said.
“Well, it’s early in your freshman year. I’m sure you’ll meet a lot more people soon,” Jason tried to assure her.
“Yeah, well, that’s sort of what I wanted to talk with you about,” Stephanie professed.
“Yeah?”
“I’m even worse at meeting guys. I get all flustered and tongue tied. I can’t seem to keep a sensible thought in my head when I’m talking to most guys. You’re different, though; you listen.”
“I’m no different,” Jason claimed. “Maybe I just initiated the discussion is all.”
“Well, whatever. I appreciate it more than you could know. Anyway, I wanted to ask you something?”
“What?”
“I think I’ve never been good with guys because all I can think about when I’m with them is sex. I read and I know most guys only think about that anyway, right?”
“Well, not all the time,” Jason mused. “Yeah, I guess, nearly most of the time.”
Jason chuckled as Stephanie continued, “I think I need to learn more about sex, Jason, but I’m afraid. I don’t know what to do.”
“Don’t you talk to your friends about it?” Jason lamented, not wanting to be cast in the role of teacher.
“What friends, remember? My roommate is a virgin too and more of a nerd than me. She’s never even kissed a guy. At least I’ve done that.”
“Exactly what have you done?” Jason asked, now deciding this could get interesting. “How many guys have you kissed?”
“Besides you the other day, if that counts, two.”
“I see,” Jason replied.
“And if your next question is did I ever get much beyond that, the answer is no,” Stephanie confessed immediately.
“I see,” Jason repeated and decided he was sounding like a jerk shrink doctor.
“So you see, my real question is, will you help me to discover sex?” Stephanie asked outright.
“Geez, Stef,” Jason called her for the first time. “I don’t know … ”
‘What was he saying?’ he thought as he was saying it. ‘What’s the matter with you? This girl wants you to teach her about sex and you’re acting like you won’t. Are you an idiot? She’s a virgin too.’
“I mean I’d be glad to help but how …,” Jason began to explain.
“I was hoping you could show me a few things,” Stephanie allowed. “I know so little beyond books and things.”
“You’re sure about this?” Jason asked.
“I know you probably have plenty of other girls and I’m not the most attractive, but I find you attractive and friendly, and I think you would know what to do,” Stephanie informed.
“Geez … I ahh … I mean … ahh,” Jason struggled for the right words.
“Please say you will do it. I’ll do whatever you say. I promise. No questions asked,” Stephanie submitted.
‘God, I’ve already got one submissive and she wants more,’ Jason mulled over. ‘This could be interesting, though. She is kinda cute with nice big tits.’
“Okay, you got a deal. When do you want to start …,” Jason began to probe.
“How about right now?” Stephanie offered.
“Ahh … well, okay,” Jason said. “What’s your first question?”
“God … I don’t know if I can do this,” Stephanie proclaimed.
“Just go ahead. Don’t worry about embarrassing …,” Jason again started.
“Can I see it,” Stephanie blurted out.
“What?” Jason asked, not sure he heard her right.
“Ahh … can I see it,” she asked again.
“You mean …”
“Yeah,” Stephanie spoke.
“Shouldn’t we start a little slower, Stef? I mean kissing or something?”
“Ahh … okay. I told you I’m no good at these things.”
Jason shifted around on the ground. It felt awkward, almost clinical, as he moved to her but he did manage to kiss her and it was nice. He kissed her again and wrapped an arm around her waist from behind. He felt a little love handle but not bad. Their kisses started tentatively, and then became longer and harder, and soon, led by Stephanie, very urgent and passionate. Jason went with her but soon broke it off.
“What’s the matter?” Stephanie asked quickly. She looked nervous as if something was wrong that he stopped.
“Nothing. I just wanted to teach you to go a little slower and more tenderly too.”
“Oh, okay,” Stephanie acquiesced.
They kissed again, more tenderly this time. Jason began to get into it, as Stephanie had nice soft lips when she wasn’t smashing them against his. After a while, he introduced her to a little tongue action. She immediate caught on and battled his with hers. She was doing it nice and passionately now. They kissed for a good long time.
When Jason’s hand dropped from Stephanie’s shoulder and down her arm, Stef didn’t notice. However, the second his hand moved to the side of her soft mound, she stiffened noticeably. She didn’t stop him, as he first thought she might, so he settled over the nipple and teased it through her shirt and bra. Stephanie moaned into their kiss but didn’t stop. Jason continued until he could feel the nipple engorged and pushing hard against her clothing. ‘It feels like a nice sized nipple,’ he thought.
Next Jason had her lie back down and they continued to kiss. He stroked her cheek and soft brunette hair. She had great hair, long and soft. It smelled of coconuts too. Jason kissed her cheeks and down her neck. Stephanie continued to groan, even louder now.
She stiffened again when Jason started to unbutton her top shirt button. ‘If she wanted to see his dick just like that then surely she wouldn’t object during this first lesson to him exposing her breasts.’ Jason thought. Jason got her shirt open but Stephanie was definitely more nervous now.
Jason wasn’t sure if she was nervous about him seeing her tits or her tummy. Her hands were folded over her bellybutton, as if hiding that area, rather than protecting her breasts from being exposed. Jason kissed down her neck and between her cleavage. Stephanie moaned but otherwise didn’t move.
“If you want to keep going sit up a second,” Jason stated, looking Stef in the eye.
She was nervous but she said, “Okay.”
Jason undid her bra snap in back and prepared himself to witness the unveiling of her tits, something he had wanted to see since the day before at the pool at her house. Stephanie had lain back down, so the bra still loosely covered most of her tits. Jason looked into her nervous eyes just before lifting the bra off her chest and over her head. Her big breasts spilled out and flapped on her chest. The aureoles were light brown and the nipples a little darker. They were the biggest aureoles he ever remembered seeing, about jumbo egg size, and they were more oval too. The magnificent nipples stuck out a full inch from her breasts. Her breasts were huge and hung down practically to the middle of her chest. He glanced up at Stef and she was watching him for reaction. He was the first male to see them.
“They’re beautiful,” Jason said, knowing it’s what she wanted to hear most, but true.
They were nice. They were not nearly as spectacular as Claire’s, but very nice. They were much bigger than Caitlin’s but not as symmetrical. The nipples were awesome though, huge and suckable. He wanted to do that first as he saw them.
“You think so?” he heard Stephanie saying in his left ear.
“Your nipples are awesome,” Jason said, bringing a smile to Stef’s face as his approval made her face light up.
“They’re not too big,” Stef asked.
“Girl, where you been! Guys love big tits,” Jason exclaimed.
“Well, I knew that but I wasn’t sure they …”
“They’re spectacular,” Jason said. “How big are they?” A question guys always wanted to know.
“38 DD,” Stephanie said.
“Wow,” Jason exclaimed.
Stephanie snickered, “You like them then?”
“Yes,” Jason said and didn’t wait but fastened his mouth to her right nipple.
The inch long nipple was much bigger than Claire’s or Caitlin’s. Lana’s and Ariel’s had been small in comparison too. Stephanie’s nipple was something substantial to suck on and he did just that. Stephanie’s hand held his head in back to her breast and she moaned with delight as he sucked. It was a new experience for her and one she immediately enjoyed.
“Oh, god, Jason. That feels so good,” Stephanie exclaimed.
“Your nipples are incredible,” Jason responded, breathing around the one in his mouth.
Jason moved between her breasts, feasting on each long nipple in turn. Stephanie’s tits were softer and hung lower than Claire’s, with the nipples more towards the bottom than in the middle, but they were still wonderful to play with. They were larger and he could hold the whole thing in his hands like a bag. He could push her tits together leaving no cleavage at all, or push them apart leaving plenty of room between them. He thought, ‘Fucking her tits could be real fun.’
Stephanie was getting extremely excited by Jason’s teasing and sucking on her tits. The new feelings coursing through her body were tenfold better than when she touched them herself. She could feel her pussy wetting and even as she neared climax worried he might think her weird for getting so wet without even being touched. She groaned and then stiffened as his right hand slid south.
Jason’s hand slid under the waistband of her running pants but then Stephanie stopped him with her hands. Jason looked at her surprised and saw the fear in her eyes.
“What’s the matter?”
“I’m afraid I’m pretty excited down there,” Stephanie stated as if that was a bad thing.
“Good,” Jason replied and immediately quelled her fears.
His hand slid down to feel the fur at the top of her pussy. It was silky and long enough for him to run his fingers through. She obviously didn’t shave or trim like all the other girls did. Jason played there a second before moving lower. Her skin was creamy white and totally without tan lines. He wondered when was the last time she was in the sun.
Stephanie’s groans were growing louder as Jason’s hand got closer to her sex. When he brushed past one side of her pussy and rubbed the soft inner flesh of her right thigh, Stef let out a long moan. Jason moved across to the other thigh to tease before moving north.
When his fingers moved across Stephanie’s pussy, she stiffened noticeably and exhaled loudly. Jason was still sucking a nipple so he didn’t see the lust filled look on her face.
Stephanie was building to the best orgasm of her young life. Sure, she had played with herself, a lot in the last two years, but nothing compared to this, a male’s touch. Her skin was like on fire everywhere Jason touched her. She was incredibly attracted to him in the first place and to have him doing this was like a wet dream come true. Everything he did was like magnified in her breasts and pussy a hundredfold now. Every nerve ending was like on steroids, ready to explode.
Jason ran his finger down the crease of Stephanie’s gash but didn’t penetrate. He was still licking her distended nipples but could see her lust tightened face. Her near growl when he touched her there told him she was very close. Even he was surprised, though, when he pushed just one finger into her inner labia and she groaned loudly as she climaxed. Her body arched off the ground and trembled as blissful waves of pleasure coursed through her like a tsunami.
“Oh, fuck,” Stephanie hissed between clenched teeth as she climaxed.
He couldn’t remember hearing her swear before and chuckled to himself. He sat back and watched the pretty young coed’s face as it contorted to the exquisite feelings emanating from her pussy. She was having the best orgasm of her life. The first orgasm she had by other than her own hand.
“Oh, geez,” Stef gasped, as she started to come down from the delicious licks of pleasure assaulting her senses.
Jason’s cock grew stiff watching the young coed cum. He was on his knees next to her but his one hand was still teasing her pussy. His fingers were soaked from her juices. He had stuck one of them deep enough into her labia to feel the blocked entrance to her cunt. He wanted in there now badly.
Shifting down, Jason grabbed the waistband of her pants and pulled down. Stephanie got the idea and lifted her ass. The pants came down her legs revealing pretty flowered girlish panties beneath. They were soaked at the crotch. He could see wisps of dark hairs sneaking out the sides near her pussy. He next grabbed the waistband of her panties and they repeated the process till she was bare below the waist.
Jason gently pushed her legs open. In the bright sun of the seasonally warm day, he could see all her charms. He was right that she didn’t shave but it seemed to make her look more womanly despite her otherwise girlish looks. Her big tits and dark bush gave him the impression of a much older woman than her eighteen years. However, she had the magical look of interest and intrigue on her face, as she watched him intently stare at her pussy, which told the true story. She waited nervously for his first reaction to seeing her sex. This was the first male reaction of any kind to her pussy.
“Pretty pussy,” Jason commented.
“Really?” Stephanie questioned, as if thinking he might have deemed it ugly.
“Beautiful,” Jason elaborated for her.
“Thanks,” Stephanie said with a broad smile painted across her face.
Jason pushed her legs further apart and settled between them. He could see the moistness of her earlier cum. Her outer lips were only slightly parted and pouty, with the inner lips still mostly closed. Only a slight wisp of her inner pink shone in the bright light. Her outer lips were slightly darker brown. Jason leaned down as Stephanie watched him with rapt interest. ‘Is he really going to kiss me there,’ she thought.
Jason used his fingers to part her inner pussy lips. She opened like a flower and he could now smell the musky aroma of her wet sex. The odor was like an intoxicant to him and he pushed his tongue into the folds. Stephanie gasped and moaned as his tongue licked her inner labia and down her crack. She was on her elbows to catch every glimpse of Jason eating her cunt.
“Oh, god, Jason,” she finally moaned aloud.
“You taste great,” Jason proclaimed as he ate her.
“Mmmm … that feels so good. I knew you’d know how to do it right,” Stef wheezed.
Jason pushed a little deeper and Stephanie reacted to it.
“Oh, fuck! Mmmm, that’s good. Oh, shit, Jason. You’re making me feel so good.”
Jason smiled at her as he spread her upper cunt. There it was. Her clit was like a beautiful pink pea just waiting to be tasted. He didn’t hesitate but instead swiped his tongue across it. The reaction from Stef was more than he expected. She shook and grabbed his hands with hers.
“Wow! Oh, fuck … ungh… oh, geez, that was fantastic,” Stephanie groaned loudly.
Jason sucked her clit into his mouth after several licks on it and around it. Stephanie arched her back and shoved her hips into his face. Her hands gripped his like in a death grip. She trembled as she reacted.
“Fuck! Oh, mother of god. Oh, Jason. Don’t stop … please don’t stop … I’m going to cum … oh, shit …,” Stephanie growled.
Jason didn’t stop but instead pushed his fingers into her pussy. He didn’t want to pop her cherry so he was careful to stay on the outside, mostly in the groove of her cunt where the moistness allowed his fingers to saw back and forth. Stef’s ass had settled back down but her trembling had not stopped. She was close again, he could tell. He wanted to taste her young snatch as it discharged her cum.
He didn’t have long to wait. His sucking and licking of her clit plus his fingers playing in her cunt drove Stephanie right up the wall. She started to buck along with the constant trembling. Seconds later she came in a mind-blowing climactic rage that made the first one seem like a distant memory, her fingers now in his hair pushing his face hard into her cunt and down on her hyper-sensitive clit.
“Sh… it …,” Stephanie grunted. “Oh, god, Jason. Don’t stop … please don’t stop … ahh …”
Jason waited for her to finally relax before removing his mouth and slowing his teasing of her cunt with his fingers. Her juices had flowed from her cunt and he now lapped them up off his own fingers. When he was done he sat up a little to look at Stephanie. Her eyes were closed and her breathing raspy.
Jason pushed his running pants down over his fully engorged cock. It was starting to ache and he could see right where he wanted to put it. A blowjob would have to wait. He wanted in her virgin pussy now if she would let him. He figured he had earned it as her teacher and for two great orgasms. He moved into position between her legs. This brought Stef’s eyes open. She stared at his monster cock for the first time.
“Oh, my god! It’s huge!” Stephanie exclaimed.
“It’s pretty good size,” Jason admitted.
“Jason, please don’t. It’s going to kill me,” Stephanie pleaded.
“It’ll be fine,” Jason stated, trying to assure as a voice of experience.
“It’s too big!” Stephanie contented. “I’ve never … I mean … it’s going to hurt too much for my first time.”
“I’ve done a few before you,” Jason professed.
“A few virgins?” Stef questioned.
“Yes.”
“You have?” Stephanie continued to query, not sure she could see that thing inside her or anyone else either.
“Yes, just relax. Let me take charge,” Jason said. He had to admit he was getting experienced at this.
“I don’t know,” Stephanie still pleaded. “You’re too big. It’s going to kill me.”
Jason rubbed the head of his cock back and forth tenderly in her slit. Her wetness from two cums and his mouth let it slide easily. The feeling felt great to both of them and Stephanie sighed despite still being very nervous. He worked it slowly on the surface and against her clit. Stephanie moaned with the contact. She stiffened though, when he pushed the head into her opening on one backward stroke.
“Oh, mother of god!” Stephanie shouted. “Jason, it’s going to hurt too badly!”
“It will hurt for a brief moment but you’ll be fine. You’re pussy is primed from your two orgasms,” Jason evenly stated, like the voice of reason and knowledge.
“It’s so big.”
He shoved forward a little, lodging the head into her cunt and encountering her cherry. ‘Here is another one for me to pop,’ he realized. Jason studied Stephanie’s face. It was painted with fear and the discomfort she already felt. He hoped this was easy for her.
“Oh, god, Jason,” Stef croaked.
“Stephanie, what are you?”
“What do you mean?”
Jason shoved hard forward. His cockhead ripped apart her hymen and penetrated slightly beyond. She screamed and hung to him with white knuckles. Jason stayed perfectly still while Stephanie endured the pain. He watched her face and the tears forming in her eyes.
“You’re a woman now, Stephanie,” Jason announced.
“It hurts, Jason. Oh, god, it hurts.”
“Just relax a minute,” he said, not moving.
It took several more minutes but eventually the worst of the pain passed. Jason still waited until the pained look began to drain from Stephanie’s pretty face. He slowly started to move. It was just a fraction at first and a little more each time if she didn’t protest. Stephanie became accustomed to his girth but he still was only partly in her. When he pressed forward, she would stiffen again. It took a while before he was able to go much deeper.
Stephanie’s pussy was extremely tight but slowly adjusted to the large intruder. Jason started slowly and kept his strokes relatively shallow for a while. Stephanie still clung to him but he could feel her relaxing a little and her pussy began to react with more wetness. He kissed her lips and her cheeks where the tears had wet them. A couple times he stopped moving and kissed and sucked on her nipples. Stephanie seemed to like that.
“I am a woman now, aren’t I,” Stephanie said out of the blue at one point.
“Yes, you are,” Jason agreed. “And from now on you’ll feel the joy of being a woman.”
“I hope so,” Stephanie proclaimed.
Jason took his time. He even sat up a little from time to time, just high enough to see over the ridge and the tall grass. He didn’t see anyone and felt they were still alone despite her earlier scream. Pretty soon he was able to establish a decent pace fucking Stephanie. She groaned but didn’t seem to want him to stop. At one point she even grabbed his sides and pulled him to her.
Jason’s dick felt incredible inside Stephanie. Her pussy was warm and wet. The tightness was incredible and he was able to go pretty deep inside her now. Part of his cock was still outside her womb but she was taking nearly six inches and not protesting. He could feel his balls churning. They were excited by this pretty girl and his taking of her virginity. He tried not to think conceited thoughts like, ‘this is my sixth virgin,’ but like any guy, those thoughts crept into his head even as he fucked her still.
He wanted Stephanie to cum for her first time. Mark had expressed to him the importance of trying to get the girl/woman off the first time so she would know the joys of sex and not just the pain. Jason kept up a pace that allowed him to simmer while bringing Stef along. It took a while but eventually she was meeting his thrusts and even pushing back. Her moans changed too from discomfort to ones of pleasure.
“Jason, it’s starting to feel good,” Stephanie said at one point, as if she was surprised herself.
“It’s going to get even better,” Jason claimed.
“Oh, god. It feels good. You’re so huge inside me. It feels like you’re up in my stomach,” Stef remarked.
Jason realized they hadn’t planned for birth control. “Stef, do I need to pull out?”
“Oh, Jason … geez … you better,” Stephanie stated.
“Okay,” Jason said, with a little disappointment in his voice.
He would have loved to stay inside her when he came. But she was right, he needed to pull out and not risk pregnancy. Cumming inside her would have been so sweet, he knew.
Jason continued at a steady pace until Stephanie showed advanced signs of her pending climax. He picked up the fucking speed when he sensed she was close. He was pretty sure he could last himself but it had better be soon too he realized. It was, for Stephanie urged him faster.
Jason was fucking her good now. Stephanie was groaning loudly and guiding him to her with each thrust.
“Oh, fuck me, Jason. Keep fucking me. It feels so good. Ahh … ”
Jason sped up and fucked her at near full clip. His own orgasm was straining his balls. He tried to think of other things but her pussy was just to incredibly tight so they never lasted long. He was thankful when she eventually exhaled loudly and bucked off the ground.
“God, I’m cumming … cumming so good!” Stephanie shouted, louder than Jason would have liked.
“Me too,” Jason gasped, trying to hold out for a few more strokes for her.
“Oh, my god … cumming …,” Stef croaked.
“Oh, fuck,” Jason yelled, and he pulled back quickly, extracting his cock from her cunt.
Stephanie was too far into her own climax to care too much, but she could immediately feel the loss of his cock from inside her. It felt like cold air was rushing into her now that he had stretched her open. Her pussy seemed sad, like she was, for the loss of its new friend. However, Stephanie could feel shots of something hot and wet between her tits and over her belly.
Stephanie opened her eyes and tried to focus down between her breasts. What she saw intrigued her immensely. The little hole in Jason’s cockhead opened and a fairly weak pulse of white viscous cum shot out onto her belly just above her pubic hair. She could see more of his cum right beneath her chin, between her tits, and a trail down to where the last shot had landed. As she watched, still coming down off her own orgasm, she saw his cockhead leak more cum into her pubes. She had missed all the forceful blasts but watched transfixed as his cock continued to leak more cum.
She had never seen a guy’s cum before other than in a porno a high school friend of hers had shown her. In real life it was far more fascinating. Her right hand stole up to her chest and dabbed tentatively into one of the cooling whitish puddles. It stuck to her finger and made a trail from the puddle to it as she pulled her hand slightly back. She rubbed it between her fingers feeling the gooey texture. ‘God, it’s his seed,’ she realized.
Jason was up on his strong arms over her. He watched as she touched the cum on her chest. She looked amazing to him bathed in his spunk. ‘Not much sexier,’ he thought, ‘than a woman wearing a guy’s cum and playing with it.’ Jason moaned softly at the end of his orgasm. He slid back onto his heels and looked up Stephanie’s body. She had cum between and on the insides of both tits. Her belly was covered and her pubes were streaked with his cum. He could see the whitish residue of her own juices around the entrance to her pussy. He didn’t see much blood, only a faint hint of pink in her cum on one side. He stared amazed knowing he had just been the first to enter that hole.
They looked at each other until they were breathing normal. Jason glanced around but still no one seemed to be nearby. He turned back to look at Stephanie and smiled.
“You alright?” he asked.
“It hurt badly at first but that was fantastic at the end. You’re good with a girl … woman, Jason,” Stephanie praised, happy to now be able to be called a true woman.
“Thanks. A little experience helps,” Jason admitted.
“Exactly how many girls … women have you fucked that were virgins?” Stef quizzed.
“Six,” Jason stated, suddenly feeling a little guilty for deflowering that many himself.
“Wow! That is a lot, isn’t it? I mean I don’t know but I would think that was a lot.”
“I think it is compared to most guys,” Jason agreed.
“Well, I guess I picked the right guy then with experience to help me,” Stephanie decided.
“I guess so,” Jason said, reaching for his pants, uncomfortable with the discussion.
“What do I do about this?” Stephanie asked, indicating the huge load of cum cooling on her skin.
Jason couldn’t think of anything else so he used his jock strap to wipe her off as best he could. It got most of it and he pulled his pants on without the strap. He shoved it into his pocket. They dressed quickly and headed back. They passed three people running, two guys and a girl, on the way back. It was doubtful they had heard anything, though, as they were still heading towards the field on the path.
They walked back since Jason no longer had anything protecting his cock from flopping about in his running pants. It gave them plenty of time to talk. Stephanie thanked him repeatedly for being such a thoughtful and caring sex partner. Jason tried to remain humble and not embellish on it too much. He was surprised, though, when Stephanie asked what’s next.
“Next? What do you mean?”
“Well, Jason. Even I know there is something we haven’t tried,” she said and put her finger seductively into her mouth.
“You want me to teach you to do that too?”
“Sure! Since you’re such a good teacher and all.”
“Well, I suppose I could,” Jason said, not believing his own reluctance.
He worried where this was headed though. He already had a submissive to contend with, two hot babes in Claire and Caitlin, he’d love to fuck Kim again, and now Stephanie practically begging him to teach her the ways of the Kama Sutra. How much could one guy handle and he was supposed to be fucking virgins. ‘Oh, god,’ he thought, and visions of that redhead at the party came to him.
“It’ll be fun,” Stephanie was saying as he picked back up on the conversation.