Sophomore Year Pt. 03

Part 3: Anal

This story includes a brief description of light S&M that you might want to skip if that puts you off.

Chapter 7: Exhibitionist & Voyeur - Patty puts on a show while driving down the freeway.

As Patty and I were driving back to school later that day, I decided to tell her what had happened. "Patty," I said, "I know it sounds weird, but I hooked up with Mark this weekend. We jacked each other off and went down on each other."

Patty's face turned red instantly. "You had sex with my brother!" she said angrily.

Keeping my voice calm and reasonable, I answered, "Yes, that's what I just said."

She crossed her arms and glared at me as she asked, "How could you?"

I thought about that and answered, "How could I what? How could I have sex with someone else? How could I have sex with another guy? Or, how could I have sex with your brother? Which one is bothering you?"

Patty got defensive, "Just answer the question."

I glanced over at her and said, "I'm pretty sure you and Clarice aren't just platonic roommates, based on some things you both said, and the fact that Clarice acted like it's perfectly normal for you to suck on her tits. That means you'd be a hypocrite if me getting something on the side bothered you, or if you're bothered by me or your brother doing it with someone who's the same sex. Assuming I'm right about you and Clarice and assuming you're not a hypocrite, what's left is you not liking the idea of me with your brother. Do you just not like your friends to be your brother's friends too?"

Patty still looked angry, but I could see I'd gotten her out of attack mode, at least temporarily. She asked me in a suspicious tone of voice, "What do you mean?"

I answered, "Mark's friend Brian told me about the time you had a fit when Mark and Rebecca were making out at a party. I think you have an issue with Mark mixing with your friends."

Patty started to deny it, but she stopped with her mouth open as if to speak. She was quiet for a few minutes before asking, "How did you figure that out? You've only known me for a few weeks."

I smiled and answered, "I like to hear people tell their stories. It wasn't hard to figure out from there."

Patty sighed and said, "I guess you're right. When we were kids, Mom made me take Mark pretty much everywhere I went. There were a lot of kids my age in the neighborhood, but none Mark's age. A year difference in ages doesn't seem like anything now, but as kids, it was huge. And we're actually less than ten months apart."

I asked, "So you didn't like having Mark around all the time?"

Patty answered, "No, that's not it. Mark has always been really sweet and fun to be around. I like spending time alone with him. The problem is, my friends liked Mark a lot. Sometimes I felt like I was competing with him for my friends' attention. That's when I started to resent him being around all the time. So maybe you're right. Maybe it is just a sibling thing."

"So you're okay if I get a little strange every now and then?"

"As long as you tell me the details."

"And you're okay with me having sex with guys?"

Patty laughed and said, "Actually, gay sex gets me hot. Last year a gay friend took me to an LGBT party off campus. I accidentally walked in on two guys while I was looking for the bathroom. They said, 'Look, we've got an audience' and continued on. I stayed to watch and left with soaked panties. Since then, a lot of times when I'm I the mood to watch some porn I'll find a gay or bi video."

I had to ask, "So what about my suspicions about you and Clarice?"

Patty admitted, "You were spot on. We started when Rebecca talked us into a Truth or Dare game that got a little out of hand at one of our naked sleepovers. We've been doing it ever since. And yes, we've both done it with Rebecca, and with other women too."

"I think Rebecca's known she's bi since puberty. When we first started noticing boys, she was the one who suggested we should practice for dates by kissing each other."

I laughed and said, "I want to hear some of those stories. Will you and Clarice show me some girl-on-girl action?"

Patty punched me in the arm and said, "You're a pervert."

"I thought that was my most endearing quality."

Patty gave me a sly grin and said, "That may be true. We'll have to see what Clarice thinks. And I'll think about telling you the story of 'The Night of the Lesbian Professors.' Now, give me some details about what happened this weekend."

I laughed and said, "Now who's the pervert."

"Guilty. Now start talking."

I went through the events of the weekend, ending with sucking Mark's cock before breakfast that morning. About three minutes into the story, Patty had her jeans down around her ankles and her top pushed up over her tits. Seeing that, I made sure to drive alongside any truckers I saw. Most of them gave us a big honk of appreciation for the show.

When Patty first stripped, she positioned herself so she was leaning against the door and facing me. After he heard the first honk she reversed her position so she was leaning on the center console with her head resting on my shoulder and her right foot was up on the door handle.

A little later we came upon a minivan. I could see a video for young children playing on the overhead screen as I pulled up behind it, but I couldn't see the kids' heads. It looked like the dad was driving.

As I started to pass them, I saw that I had guessed correctly and the kids couldn't see down into our car, so I pulled even with the driver's window. The dad looked over and caught a clear view of Patty. He got a big grin on his face, and he kept glancing back and forth from Patty to the road in front of the car.

As I glanced over, I could see that the mom had figured out something was up and was asking her husband what was going on. He said something to her and nodded in our direction. She leaned over towards him to look, but I think she could only see Patty's tits from her viewing angle.

I mentioned this to Patty, and slowed down a little to put Patty's window across from the mom. Patty smiled as she sawed three fingers in and out of her pussy and mauled one of her tits with her free hand. The mom smiled and said something to the dad that I assume was a promise of things to come, based on the happy grin on his face. After a minute, I continued passing them and drove on.

As I finished my story Patty saw a sign for a rest area and told me to pull off, so I did. I assumed she needed to use the lady's room but when we got into the building she dragged me into the family restroom for a frantic quickie. Of course, I had to clean her up, and she sucked my cock clean. As we walked out of the cubicle, we saw the family walking in. The small children I had glimpsed in the car were two preschool aged girls. The parents spotted us, and the mom blushed.

Patty approached the family and spoke briefly to the mom. As Patty leaned in to talk to her, I saw the mom's eyes flash as she gave Patty a knowing smile. Then the mom said something to the girls, and Patty took them by the hand and led them into the women's rest room while the mom and dad walked past me into the family restroom cubicle. A few minutes later, Patty and the girls came out of the rest room, and shortly after that the mom and dad came out of the cubicle. We all went to our cars and got back on the road.

I asked Patty, "Do strangers always leave you in charge of their children while they grab a quickie?"

Patty laughed and said, "That was Bonnie. She was a TA for one of my classes last year. She's from my hometown, so I caught rides home with her and her family a couple of times last year. Sitting in the back of their minivan with the girls gave me a chance to get to know them, so I wasn't a stranger. Bonnie told me that her husband, Mario, had a thing for me after those trips, and she said that after today's show he might divorce her and come chasing after me."

We arrived at school a short time later. Since Patty had worked all weekend, she was behind on her homework. As soon as we got back to school she gave me a kiss and pushed me out the door so that she could work on catching up.

I went back to my room and texted Mark to let him know I had talked to Patty. He called me back within minutes to see how it had gone. I told him she was pissed at first, and now she's cool with it, and even thinks it's kind of hot.

I also told Mark that I thought Brian would be open to picking up where they left off. He asked why, and I told him about Brian checking him out while we talked at the party, and his tone of reminiscence when he talked about what they'd done together. I finished by saying, "I'm sure he'd never make a move on you, but I'm also sure he'd love it if you got back to being close friends again, even if you don't hook up."

As Mark hung up, he said, "I'll think about it. I haven't had a good friend like Brian since then."

Chapter 8: Anal - Clarice talks about her introduction to anal.

Patty finally got caught up on Tuesday afternoon. As we met for dinner, she said, "I hope you have time to come up to my room for dessert."

When we got back to her room, Clarice was there. She greeted us by saying, "I was wondering when your gay boyfriend was gonna show his face again."

I shouldn't have been surprised that Patty had shared the details of my weekend with Clarice, but I still started to voice my offense at the "gay" comment. Then I saw the twinkle in Clarice's eyes. I asked Patty, "Do you keep any secrets from this girl?"

Patty laughed and said, "I haven't told her about my fantasy of having a three-way with her and her mom yet."

Without missing a beat, Clarice said, "No, you haven't, but now that I know I'll have to run it by her."

Patty looked at Clarice and asked, "You called him gay. Is he gay if he's never been fucked in the ass?"

Clarice considered that before answering, "Playing with another guy's dick and sucking cock are pretty gay. Butt fucking is just the final bonus."

I had to interject at that point, "I'm pretty sure I don't want to play the bonus round."

Even though I stand a full head taller than her, Clarice somehow managed to look down her nose at me as she said in an icy tone, "Why not?"

I was a little surprised at her question and her tone since it seemed obvious, but I answered, "It sounds kind of gross, and I'm not into pain."

Clarice said rather stiffly, "So you really don't know anything about it."

Now I was feeling defensive. I said, "What's there to know? It seems obvious." in as cold a voice as I could muster.

Clarice threw up her hands, made a sound of exasperation, and launched into a lengthy explanation about the nerve endings in the rectum, how anal sex stimulates the prostate, how the clitoral nerves extend into the rectum, how the sphincter muscles are designed to relax to allow passage of large objects, and how the colon is generally clean and can easily be made cleaner. She finished by saying, "It's fun if you do it right."

That last statement begged the question, "How do you know?" So I asked.

Clarice admitted, "I've had a lot of anal sex, and I really like it."

Patty chimed in at that point, "So you've been keeping secrets from me."

Clarice looked at Patty and answered, "I guess. I used to have the same attitude as Ian, so I was maybe worried you'd think it was too out there. I used to do it with Bill."

Patty said, "Bill? He's 6' 6" and built like that guy, Shaq."

Clarice confirmed, "Yep."

Trying to picture tiny Clarice with a guy like that caused me to blurt out, "You would think a guy that size would have a big cock."

Clarice gave us a shit eating grin and said, "Oh yeah!. I measured it once. He was eight inches long, and when I wrapped my hand around it, my fingertips wouldn't touch."

"Holy crap," I gasped, "he couldn't possibly have fit that up your tiny butthole."

Clarice shook her head and said, "That's what I'm trying to tell you. He did, and I liked it."

Patty was losing patience, "Alright, spill! Let's hear the details!"

Clarice looked at the two of us sitting there in anticipation, and began, "Bill was the second guy I slept with. Connor was the first. Patty, you remember Connor, right? I lost my virginity to Connor after we'd been dating for three months. The next day I overheard him bragging about getting my cherry to a group of guys in the cafeteria. I dumped him on the spot."

"Bill had been in the group listening to Connor, but when Connor started to brag, he got up and left. Later he overheard me blowing up at Connor, and he felt bad for not having said something. He came to me and apologized for not telling Connor to keep it to himself. We started dating a week later."

"Bill wasn't a virgin, so we had sex on our fourth date. I was sure my mom wouldn't sign the consent for me to be on the pill, so we had to use condoms. That was the problem."

"When Bill wore a rubber, he had a hard time getting off. The first time we had sex, he pounded me for an hour until I was sore, and I still had to jack him off while I sucked on his cock head so that he could cum."

"The next time, we tried not using a condom and having him pull out, but you know how hard that is for a guy. Bill was nervous he wouldn't pull out in time. I was nervous about that too, and about the fact that the guys swimmers can get out of the gate even before he cums. The nervousness ruined it for both of us, so we decided to stick to condoms."

"We made a date for one Friday night after a basketball game. The dance team performed at half time, and as I was grabbing my stuff from the locker room after our performance, my friend Roxie said, 'Come on, Cassie's saving us seats.'"

"I told her I couldn't because I had to go to the drug store. She asked why, and I told her I was trying to find some condoms that wouldn't dull the sensation too much for Bill. She had told me that she and her boyfriend use condoms, so I thought she might have some suggestions."

"She surprised me by saying, 'We don't have that problem anymore. He fucks my pussy with a condom on until I cum, then he takes it off and fucks my ass until he cums."

"My reaction was similar to what you said earlier. Roxie told me, 'As long as you take it slow and do some preparation, it's great.'"

"I asked her, 'What do you mean, "great."'"

"Roxie said, 'I usually cum again while he ass fucks me. Having an orgasm with a cock up your ass is a completely new experience. Usually, I diddle myself while he fucks me from behind, but every now and then I've actually cum without touching my clit.'"

"That sounded intriguing. I asked her, 'What did you mean by "prep."'"

"Roxie asked me, 'Do you want me to show you?'"

"I said, 'Here? Now?'"

"Roxie said, 'Sure. We're going out after the game, so I need to get ready anyway.' She grabbed her gear bag and started walking towards the rest room next to the locker room, waving for me to follow her. When we got in there, she pulled a black rubber bulb with a long red tip on it out of her bag, along with a squeeze tube and set them by the sink. She said, 'This is the first step,' as she kicked off her shoes and stripped off her panties and tights from under her dance skirt."

"She unscrewed the tip from the bulb, ran water into the sink until it was warm, and then filled the bulb and screwed the tip back on. Picking up the tube and handing me the bulb, she said, 'Follow me," as she ducked into the handicapped stall. Once we were in the stall, she showed me step by step how she used the bulb to clean herself, repeating the process three times. It was weirdly intimate to watch."

"After the third time, she had me look into the toilet bowl before she flushed. 'See, there's nothing nasty left in there.'"

"She told me to stand behind her so I could watch what she was going to do next."

"As I moved behind her, she bent over and flipped up her skirt again. She lubed up a finger, then reached back and rubbed the lube around her asshole before trying to push her fingertip into her ass. When her asshole wouldn't open, she added more lube and repeated the rubbing and probing. This time her finger went in up to the first knuckle. Lubed her finger one more time, and when she pressed it into her hole that time, her finger went all the way in."

"'You have to be nice to your sphincter. If you romance it a little, it'll open up for you and you can have your way with it,' she said. She fucked her finger in and out of her asshole three or four times, and then pulled it out."

"She lubed two fingers and repeated the process with both of them. Then, she took a piece of toilet paper, wiped off her finger, and said, 'Do you want to try it now?'"

"I knew there was a big difference between a finger and Bill's cock, but I figured it might be worth a try, so I said, 'Yes.'"

"Roxie helped me clean my asshole. Then she told me what kind of lube to buy. She said, 'Have Bill play with your ass tonight, but don't let him fuck you there yet. Have him work up to fitting two fingers into you. A rim job is a great way to start, especially when you're nice and clean like now, but don't be surprised if he's a little squeamish about it. Tell me how it goes, and then I'll help you with the next steps."

As Clarice was telling her story, the three of us had gotten undressed. Clarice was in her usual spot in the bean bag chair, idly running her finger over her pussy. I was slouched on the futon with Patty draped over me, my cock lodged in her cunt. She was twisting one nipple and I was running my hands over her thighs, ass and back.

Clarice continued. "Roxie spent a few more minutes giving me a tutorial on anal sex, then wished me luck. As we left the locker room, Roxie recommended a brand of condoms that she said would help Bill feel more stimulation. I ran out and bought a box and a tube of lube, returning just as the game ended."

"After the game, I told Bill about Roxie's suggestion. He was all for the idea. Apparently, anal sex was one of his fantasies, but he never brought it up because he thought with his size no girl would go for the idea. I said, 'We're gonna have to go one step at a time,' and he was okay with that. He said that he'd read a lot about anal sex and knew what Roxie was talking about."

"Bill drove a full sized SUV. He told people that he needed the headroom, but all of the room in the back was also a plus. He usually drove around without the middle seat, and he had the windows tinted dark. With the four-wheel drive, he could go places where the police wouldn't show up, shining their flashlights in the windows. We joked that it was his 'Shaggin' Wagon.'"

"We got something to eat, then drove to a remote, wooded area and settled into the back seat. The condoms did help, but I still ended up giving him a blowjob. He surprised me by asking me to play with his ass while I blew him. I reached into my purse, pulled out the lube, and asked him if he wanted me to use some of that. He responded with an enthusiastic, 'Yes.'"

"I lubed my finger and ran it up his ass crack. He obliged by spreading his legs wide and reaching under them to pull his ass open. I started licking his head like an ice cream cone. As I ran my finger over his asshole, I pushed gently at the opening while I wrapped my lips around his knob and fluttered my tongue under the rim. Then I resumed licking and rubbing."

"About the fifth time I repeated this, I felt his ass open up and my finger went in to the second knuckle. I held it there while I forced my mouth down over the top four inches of his length. I applied as much suction as I could to his cock, and continued to flick my tongue over the veins on the underside as I slowly let him out of my mouth. At the same time, I wiggled my finger and fucked it in and out of his asshole. I was looking into his eyes and I could see sweat on his brow as he took long, slow breaths."