Tim in College Ch. 02

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Tim reconnects digitally with a busty old friend.
6.8k words
4.83
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12

Part 2 of the 5 part series

Updated 04/21/2024
Created 02/20/2024
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2 - Good Girls Don't Do That - Part 1

"How's it going?"

The words popped up on my computer screen suddenly one cold night in February of my first year of college. I looked at the words, then at the name, and I paused. It was a name I knew, a name I hadn't thought about in months. A name I had history with.

I was conflicted. Though my first year of college had been a good new experience over all, sexually it was a barren waste land at that point. I had arrived thinking college was going to be a nonstop fuck fest, but outside of one (albeit amazing) handjob from Anne-Marie, the girl across the hall with whom i had developed a close, but purely platonic, friendship with afterwards, my only sex partner had been my own hand.

This message didn't promise anything different, but given the history I had with the sender, it definitely intrigued me. It came from a girl who frequented the church I went to back home. A girl with red hair, and the biggest tits I had ever seen. A girl named Rachel.

Rachel and I had always been flirty, especially while talking online, and after accompanying her to her senior prom, we became a little more than that. In a backyard tent at the after prom festivities, I got to feel those tits first hand, touching her body, running my fingers all around her wet, 18 year old pussy until she exploded. She would return the favor, and for the very first time in my life, a girl would use her hands to make me cum.

And cum I did, making quite a mess all over her fingers, and getting an errant shot on the curve of her thick breasts. But unfortunately this is where the enchantment ended. As the insanity of sexual desire left, things got awkward, and the reality of my bodily fluids all over her hands elicited an almost panicked "Ew, GROSS!" from her.

It was simultaneously the best and worst night of my life up to that point. It was my first sexual experience, and it ended in disgust from my partner. Maybe not a big deal to the more worldly, but to my virginal, 18 year old ego it was devastating.

Things had more or less stayed awkward between us after that, and I thought we had gone our separate ways forever after the summer ended, but the world was smaller than ever, and technology reopened that door with three small words and the press of an enter key.

"Not bad, you?" I wrote back rather coolly, testing the water between us.

"Same," she replied, "just trying to get through this first year." There was a pause, and then, "long time no talk, huh?"

"Yeah," I typed, smirking to myself. The last time we had seen each other had not been amazing, and I wasn't sure where she and I stood. We had been on a church camping trip where she had brought her then-boyfriend, and made quite a display in an attempt to make either he, or I, or both of us jealous. It ended with me yelling at her, and her boyfriend breaking up with her--not the most pleasant way to spend a summer weekend.

That was the last time I saw her that summer, but despite all the other experiences I had with all those other girls, I'd be lying if I said the thought of her red hair and big, luscious tits didn't pop into my head from time to time. I thought of how things might have gone differently if I had had more experience. If I had more control over the situation.

We made pointless small talk about school and classes, but I wasn't giving her much. I could tell she was dancing around something she wanted to say. Finally she came out and said it.

"Hey, um...I wanted to tell you something. I wanted to apologize."

"For what?"

"For the way I acted last summer, especially on the camping trip. I felt like I was out of my mind, and I ended up treating some people pretty shitty."

"It's ok," I said, sincerely, "I think we were all trying to process a lot. I know I was." It was honestly nice to hear her admit it, and any resentment I had was gone. But what was left was questions. "Out of your mind how?"

There was a long pause. It intrigued me immensely.

"With certain...urges..." followed by a nervous "lol."

"Haha I see." Very intriguing indeed. An excited surge shot into my cock. She was being coy, but I knew exactly what kind of urges she was talking about.

"You're telling me you weren't?" She was definitely opening a door, and our distance, plus my own sexual frustrations, gave me zero pause in flinging it wide.

"Oh I was," I admitted, leaving out any mention of my outlets for those urges. I thought for a moment, and then decided to push further with the honesty, to see how she would react. "As I'm sure you could tell that night after prom."

"Yeah," she wrote, followed by a short pause. "I think that was ground zero for me too."

Interesting. I decided to change tack, but continue my prying.

"So how come Devon didn't want you to touch his dick?"

Another pause, even longer this time. I had clearly struck a chord.

"What do you mean?" she wrote back. I knew she was playing coy. I pushed forward

"I saw you two in the woods on the church camping trip. When you broke up. After you jerked him off."

Another pause.

"That never happened," she said, followed by a phrase that soon enough would come to be a sort of mantra of coy denial for her, "good girls don't do that."

"He has a huge dick, I can see why it would be so frustrating." I was prying, fascinated by her denial, but trying to show her I was on her side. There was another long pause. I wasn't sure if it was working, so I followed up. "I have to assume if he didn't want you touching him, he probably wasn't touching you either, right? That sucks."

I knew it was an inflection point. This was either going to bring her in closer, or drive her away completely. My hand drifted down to my cock and absentmindedly began squeezing it as I waited for a response.

"That's a very personal question," she typed, finally.

"It is. You don't' have to answer it if you don't want to,'" I said, giving her an out.

"What do I get in return for sharing that kind of information?"

I thought about it for a minute, and then a solution came to me. One that I had used very successfully with my friend Tara any time we wanted to talk about more personal matters.

"What if we make a game of it?"

"What kind of game?"

"Truth or dare."

The longest pause of the conversation. I wasn't worried about her answer. I knew that if we had made it this far, she was game, she just needed a little bit of cover. She WAS a good Christian girl, after all...

"Ok," she said finally, "sounds fun. Truth."

I smiled, and felt my cock harden in my hand.

"Did Devon ever get you off?"

"No," she said almost immediately, "He got close, the few times he touched me...a lot of them got close...but no. I think that's what made me go so nuts. Truth or dare."

A lot of them? Well this just got very interesting.

"Truth."

"Did you and Christine have sex on the camping trip?"

Oh she was all the way in.

"No," I said, deciding to use her own words against her, "good girls don't do that :)"

"Have you ever had sex with Christine?"

"Those aren't the rules! Truth or dare?"

"Ugh, fine. Truth."

"Tell me about 'the others.'"

"After prom night...something sort of snapped inside me and with all the summer parties I just...well, let's just say I learned a lot." My mind was starting to swirl with visions of all the possibilities of what that meant. "Truth or dare."

"Truth."

"Was prom night...your first experience with a girl?"

"Yeah."

"How was it for you?"

Now it was my turn to pause. I let the follow up question slide, and considered how to respond. Whether to be only cordial and complimentary, or to tell her the truth.

"Well," I began typing, then decided on the truth. "It was amazing...until it wasn't."

"What do you mean?"

"It was amazing--YOU were amazing--but when it was over, you shouted 'ew, gross,' and kinda ejected out of the situation. It didn't really do much for my self esteem."

"Yeeeah, I had a feeling that's what you meant," she typed back fairly quickly. "The truth is, you were only the third guy I had ever done THAT to, and the first one I ever finished."

"Seriously?"

"Yeah, I had never had to deal with the, you know....mess...before, and I kinda freaked out. I was still figuring things out--still AM figuring things out. And I mean, honestly, it IS pretty gross."

"Haha, that's fair--just a hell of a time to express that!"

"I know, I know, I'm sorry, what can I say. But I promise I'll never call YOURS gross again, ok?"

My cock flexed in my pants as I agreed and accepted her apology.

"Listen, I gotta run--I'm glad we talked," she typed, "Hope we can do it again soon."

"Yeah me too," I sent back before quickly firing off a final question. "Wait, before you go. Truth or Dare?"

"Truth."

"How was that night for you?"

There was a short pause, a response. Not words, but symbols:

" :D "

I smirked. My cock twitched again. We each said goodnight, and then I fell back onto my bed, hard cock in hand, and stroked myself hard to the thought of Rachel's hands on me that night, stroking me, her big, milky breasts hanging over me, pressed tight together by her arms. I jerked myself fast and came hard, just as I did in the picture in my mind's eye. Only this time, when my cum hit her skin, Rachel didn't react in disgust. This time she just smiled.

****

This digital reunion became the start of frequent online chats. We talked about any and everything. It was nice to be able to decompress from all the newness of school with someone I was familiar with. We talked about friends, roommates, classes, family back home, all cordial, all above board. But it became pretty clear, pretty quickly, what was really driving us. As we chatted into the night, eventually the casual chit chat would start to get a little more personal, and eventually one of us would ask the question.

"Truth or Dare?"

"Oh here we go again," she typed back feigning incredulity.

"Oh so you roll your eyes whenever I start, but it's fine when you start? I see..." I said jokingly

"I never start!" she wrote back.

"What!" I wrote back, as this was very untrue. "Just the other day you started it off by asking me if I ever measured my dick!"

"Well I do it for educational reasons, I know YOU just want to hear smutty stories!"

It's true that that instance in particular was educational, as I learned from my response question that those amazing tits of hers were size 36G.

"Oh yeah? Do you remember what your last question was that night?"

"Nope."

I knew she was lying. Our little game that night had gotten increasingly teasing and blue, and my cock was tight in my pants by the time she asked her final question, which was a technically unfair double question of had I ever had a blowjob, and what was my first time. I told her all about my prom, and about my prom date Steph sucking my cock in the limo. Then she surprised me with four words I wasn't expecting:

"Where did you cum?"

"In her mouth." I wrote back, then doubled down on piquing her interest with "she swallowed it."

"Gross," Rachel wrote back

"Hey!" I exclaimed, teasing her about her recent promise.

"No, not you, swallowing. The whole...thing."

"You never swallow?"

"No."

"So what do you do when a guy cums in your mouth?" I casually stroked my cock as I asked.

"They don't."

"But you HAVE given blow jobs before?"

"Maybe I have, maybe I haven't," she coyly answered, "but they are not allowed to do that. No one is."

"Not even me?" I said, casting a question fueled completely by the hard on in my hand, a question that clearly caught her off guard.

"What?"

"You said you don't let guys cum in your mouth or swallow because it's gross, and you said mine ISN'T gross, so..." I followed up with one of the smiling emojis she was so fond of.

"You're ridiculous," she protested mildly, and then came that phrase again, the one that was becoming so emblematic of Rachel's conflict over her sexual urges, "good girls don't do that."

"Mmhmm..."

She sent me an emoji of an inquisitive face, then changed the subject. My cock stayed hard for the rest of our comparatively tame conversation, and after signing off, I stroked myself until I exploded, thinking about cumming in Rachel's mouth, and the fact that despite her hemming and hawing at whether she'd let me cum in her mouth...she never said no.

"Haha you are full of shit!" I teased her, after trying to remind her of that encounter.

"TRUTH--Just ask your question!" She said back

"It's actually kinda related to that last conversation." I teased.

"Here we go--what is it?" she teased back.

"When did you give your first blowjob?"

"Mmhmm, I knew it..."

"Haha, WELL?"

There was a short pause, followed by a short answer.

"It was the day after prom."

I shifted myself in my seat. The thought of Rachel tasting her first cock just hours after our experience in the tent together thickened me up quickly. Much like the other church girls I'd met, this one had a wild side, and I was very curious to hear about it. I waited for more, but nothing came.

"That's it?"

"I answered the question! What else do you want?"

"I told you ALL about mine the other night!"

"What do you want to know?"

"The details! Who, what, where, when, you know, the details!"

"Ugh, fine," she weakly protested. "The next day we all went to the beach. There were some other kids from school there, and we were all hanging out having a good time. I was flirting with this guy Marcus, from the track team, and we were just chilling."

"Drinking?"

"Maybe a little. So we were feelin' each other, so we sorta snuck off somewhere private and started fooling around."

I took a moment to make sure all the doors to my room were locked, then slid my hard cock out from my pants before asking my next question. "Fooling around how?"

"Gotta know everything huh?"

All I could respond with was a smiling emoji.

"We were making out, and he started touching me, but he didn't know what to do, which was...frustrating to say the least. He just kept rubbing me and getting me all worked up, and then I just reached over, pulled it out, and, well..." There was a pause before she continued. "Something came over me, and I just really wanted to try it, so I leaned over and put it in my mouth."

"Did you like it?" I typed with one hand while stroking myself, thinking of Rachel, big, porcelain tits out, putting a cock in her mouth for the first time. I silently pitied poor Marcus for not knowing what to do with those tits. I hope he pitied himself too.

"I didn't hate it, but I don't know if I liked it. Not that first time, anyway."

"Do you like it now?" I continued probing, trying not to give away how hot her story was making me.

"It's fun. But I wasn't totally sure about it that first time, so I just sucked him a few times and then finished him off with my hand and that was that." Her coyness was gone now, and she apparently was comfortable enough to tell me the truth, at least at this moment in time.

"Did he return the favor?"

"Nah, it was just over after he was done. We went back to the party and that was the last time I saw him that summer.

"But not the last guy?"

"Now that's a completely different question!" she finally stopped my extra curricular inquiries. "My turn--truth or dare."

"Truth."

"Have you hooked up with anyone since you've been at school?"

"Just one," I said, telling her the truth, "it was the very first weekend. It's been an excruciating dry spell since then." I decided to attempt another extra curricular question. "Have you?"

"Not since before winter break. I was sort of seeing someone, but it didn't work out."

This was interesting. It was the first I had heard, and I had a very pressing question on my mind.

"Truth or dare?"

"Truth."

"Are you still a virgin?"

Ever since we had started our late night chats, I had been trying to gauge the answer to this question. I had learned first hand that church girls were total freaks, but their boundaries varied quite a bit. When I started hooking up with my dear friend Christine, the pastor's daughter, she put a rule in place that she could touch me anywhere, but I could only touch her from the neck up. This took full sex off the table, in an attempt to preserve her virtue that made sense for her, but that meant that almost everything else was on the table, and allowed her to indulge in her favorite kink: sucking my cock and taking a big faceful of my cum. It made sense to her, and I wasn't one to argue.

Conversely, there was Talia, another "good Christian girl," who, unlike Christine, was more than willing and extremely anxious to experience everything sex had to offer. She gave me her virginity, and I gave her my cock in every manner she wanted, until a pregnancy scare ended things between us.

And that's not even to mention what I knew about my step-mom's sex life, or the sex life of her best friends, all of whom were regular church goers. The point is, I knew well enough that when it came to religion and sex, there were many interesting caveats, conditions, and kinks that could come to light. Rachel was clearly not one who felt the need to be completely chaste, and I was very curious to see where her own, personal line was.

"Yes. No sex till marriage."

"But the other stuff is ok?" It wasn't meant as a judgment, just curiosity.

"No sex till marriage."

Rachel was turning out to be a very fascinating case, as I didn't think there was any real conflict in her, not like there was in Christine. I could tell, even at this point, that Rachel had no real qualms about sex, she was just putting up a front of perceived virtue. Christine was constantly in conflict between her faith, her upbringing, and her lustful desires. Rachel's "good girl" front was just a routine--more of a social perception thing than anything else. She clearly liked hooking up with guys, liked sucking cock, but just didn't want to actually admit it to anyone. But at the same time, she clearly had her own religious-based limits on pre-marital sex. Christine's no sex rule was a final backstop, the absolute limit she'd allow herself to sin up to. Rachel's interpretation, on the other hand, seemed more to be that anything less than sex was ok and fair game as long as her reputation remained intact.

"Truth or dare?" she asked me.

"Truth." I said, still nursing my hard on, waiting for the next bolt of endorphins

"Are you?"

"No," I answered truthfully.

"Who'd you lose it to?"

"The prom limo girl."

"At the prom? Or later?"

I could tell she was fishing. She wanted me to tell her the story, but didn't want to ask for it. So I obliged her. I told her about how Steph was my step-sister's best friend, and how we had been hooking up ever since the prom, and then one night I went up to her place to talk. About how the night before my graduation we fell asleep together, about how she woke me up in the middle of the night with her mouth, and then how, like an erotic angel, she glided over me and slipped me inside her.

"Damn," she said, "that's steamy. Did you use a condom?"

"No."

"Where did you cum?"

This was the second time Rachel had asked me this. For someone who claimed to be grossed out by it, she was sure curious about where it went.

"Inside her."

"Was that the only time?"

"No, we continued our thing for a while. We had sex a lot." I paused and then offered something she didn't ask for. "Never with a condom. She was on the pill."

"Was she the only one?"

"I think it's my turn!" I said. Now it was my turn to play coy with the details.

I was formulating my next question when Rachel suddenly called an end to our proceedings. Her typing seemed rather flustered, and she left abruptly. It could have been interruption from her roommate, or something else, but as I leaned back and stroked myself, I wondered if it was something else. I wondered if she had been touching herself like I was.

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