Chapter 239: Karen in The Lead

I guess they feel I would be more comfortable with someone close to my age as a chaperone, even my chaperone was a girl?

“Hey. My name is Karen. I’m your chaperone for today and tonight,” she said sweetly, as she hooked her arm through mine. “Before you ask, I already got an email from someone that said I wanted to be your chaperone for any number of reasons, the least of them being that I’m only two months older than you. While our campus is one of the safest in the state, the campus police advise us not to keep anything in our cars. They made me tell you that before they said I could give you the parking permit. Very early this morning, the Chancellor let me know that something came up, and he won’t be able to meet with you until two. His admin said he took the time to read through the very detailed report from the college you visited yesterday. I have our list of who you are to meet and when. If you’re as smart they hinted, I hope you won’t feel like they are just wasting your time with what now seems to be merely a formality to whatever you have planned out. Lunch for you will be at the faculty club with a few professors. If we don’t stop somewhere, we have time to drop off your stuff in my dorm room before you get to sit with me in my only class today. The Chancellor thought you would find it enjoyable as he heard you know some languages. My Asian language teacher behaves like he believes he is fooling his students with his knowledge of the languages he teaches.”

They sold you out. I know more than some languages. I know them all or will a few seconds around someone how speaks them or something written in them.

I only had a backpack and a bag with clothes. We drove to Karen’s dorm and parked in one of the long-term visitor parking spaces for someone with the hangtag she gave me.

We had a bit of fun, which she did tell me to expect when we were passing the front desk. Karen only being sixteen required her to be in the “virgin vault” dorm that had separate entrances for the male and female towers. No one of the opposite sex was allowed in the tower of the opposite sex unless they were a parent, and that was only during the two days where everyone moved it.

The woman at the desk knew Karen on sight and said, “Sorry, Karen. You know the rules. No males in the female tower.”

“Caitlin, there is a form from the Chancellor and head of the housing department granting permission for a David Jones to have access to the female tower and reside in my room, providing he is in my presence and not being a nuisance. There is a picture attached. I’m his babysitter because I’m two months older than him, and I’m the only student under eighteen on campus this semester,” Karen told the girl behind the desk. “You’re the one that told me about his big scandal last summer involving the governor’s program where the three of the same-sex minor males paired up with an adult male student. It isn’t like I need to worry about him taking liberties with my virtue. Three trusted friends, from my freshman year, told me all about him. If I want to study human biology with him, I have to bed the instructor before he starts the lessons.”

Interesting. I wonder who talked to Karen about me?

Once Caitlan verified the paperwork with her boss, she did something to the computer behind the counter, took my picture, and handed me an ID badge. The back had mouse type while the front had my image and Karen’s, some special note that it was valid for entry into the female dorm, floor seven, room seven-sixteen. I could only go into the female tower when Karen was escorting me. I had to have it around my neck as well as sign in and out like Karen. Given the uniqueness of the situation, our curfew went until nine PM, instead of eight.

Interestingly, it says she must escort me into the female tower, up to her floor, and into her room. I see nothing requiring Karen to accompany me around the floor, or anywhere in the dorm after that.

As soon as we stepped off the elevator, I saw two girls with towels around their hair carrying a basket of shower supplies and wearing shower shoes. That is all they had on. The women were startled to see a male on the floor. Karen pointed to the badge around my neck. I decided to be me.

The first one had been wearing a bra two cup sizes too small and needed a band size six inches larger. Around the woman’s waist, and going between her legs, she had a deep, angry-red impression from wearing a size two panty instead of the size six she needed, now that her body had filled out. The girl with her had the cup and band size the first one required, and she was also a size six.

To the second girl, I said, “Can you help your friend out with letting her borrow a pair of panties and a bra until she can go buy some of her own? The twenty-eight-A bras she has from last fall must be hurting her a lot, even with the hook extender. One look at her hips tells me that her size two panties aren’t cutting it either, when she wears panties at all since all she has must be way too small.”

“Do you even have more than two pairs of the size two that aren’t falling apart? I’m sure your period panties, and boxers you stole from your brother, are being held together with bobby pins,” I asked the first girl, who had been doing good holding back the tears until I mentioned the bobby pins.

I took her basket of soaps and gave them to Karen before I leaned down to pull the woman’s arms around my neck and arm up under her skinny butt. She automatically put her legs around my waist when I stood up. Her face was buried in my shoulder as she cried.

When we got to her room, her roommate jumped up to see what was wrong. The second she saw, I was a guy she reached for her cell phone. Even with her roommate in my arms, I was fast enough to get it from her and put it back to where she picked it up.

I wasn’t paying attention to her naked shower mate, so I didn’t see her leave to go to her room, throw on some loose shorts, and bring back a pair of panties and a bra. Once the woman I was holding calmed down enough to let me put her down, I had the panties pulled into place and was adjusting the straps on her bra before she could finish blowing her nose. I moved her over to face the full-length mirror on the back of the door, which someone had closed at some point.

The three women in the room watched me like I hawk as I put the woman’s hand down inside the panties. I held her wrist to show her that she now had plenty of stretch in the panties, now that they were the right size. I then put one of her feet on a chair and reached between her legs. Her roommate again picked up her cell phone and dialed 911 but didn’t hit enter. Her phone ended up powered off in the pocket of her robe before she had any clue what happened. I hooked the woman’s fingers inside the leg hole and guided her fingers to see there was even room down there.

“With your body shape, a size seven would just have enough elastic to stay around your waist, but here would be huge gaps in the leg holes of your panties,” I told her as I pulled her finger from inside her panties where they were exploring on her own. “I know bras are expensive, but if you can find one of the underwear clearance outlets, you can find comfortable bras that even let you slide the cups around on the band to make them fit better. You probably want to also ask the ladies for the bras padded for girls that have nipples that are always partially erect, as yours were even as you cried.”

I smiled to her as I said to her roommate, “If you stand up, take off your robe, and let me show you something, I will tell you where I hid your phone. We have two other women here to call the police or scream rape if I do something inappropriate. Did I touch your roommate in anything other than chastely?”

“He doesn’t have tome to do anything anyway. We are going to have to run to my class if we stay in the dorm much longer,” Karen commented.

The girl in the robe looked a bit worried, but once her roommate told her to trust me, the girl got up and removed her robe. I didn’t laugh but wanted to when I saw she had the opposite problem to her roommate. She was wearing a thirty-two-B and size four panties. The bra had carefully crafted latex inserts, and she had made small stiches around the leg holes and waistband of her panties to make them stay up on her straight hips.

I didn’t ask as I found the underwear drawer for the skinny girl’s roommate. Inside I was surprised to find two new, unopened packs of size three panties and four new twenty-eight-A bras. The bras I knew from the outlet store. They ran a half-cup smaller and had a one to a two-inch variant in band size, but it was elastic so it would fit the size printed on the box.

The straight hipped girl told me her name was Mary. She said she wasn’t about to let the first boy she let see her in her underwear without at least knowing her name.

“I’m David. I hope you don’t mind that I’m going to be the first boy to see you naked too,” I told her as I quickly stripped off her bra and panties before she could react.

She was wearing the size-three panties, and I had the twenty-eight, half A-cup sized bra on her before her brain had processed what I had done.

I pulled out the top of each bra cup, reached in gently to adjust her small breasts to sit correctly, and said to the skinny girl’s roommate, “Wherever you got these bras, you need to shop there. They pulled this brand from stores because this style went between a half-cup and two full cup-sizes smaller than printed on the box. It is great that you have these because I would have found these specifically for how perfect they are for Mary. She is too big for a training bra and too small to wear a normal a-cup without stuffing it. Has she told you that even that her breasts would look amazing through her shirts if she went topless, her nipples are way too sensitive to do that? She came twice and now needs to change her panties, while I did my best to adjust her breasts without causing her to get off. At least it was only twice. If I didn’t already know what to look for, she would be on her back with her legs spread, trying slip of the peak of a much taller mountain.”

“Sorry. Mary. If I had known I was going to be the first guy to cause your first two orgasms, that you didn’t give yourself, I would have warned you. I should have realized it from the softer latex you had inside your molded breast enhancements. I’m probably being an ass to not even think of asking, but were your orgasms at least nice ones?” I asked her.

No. I’ve been enough of your firsts already today and Karen has a class.

Mary stripped quickly and started trying her best to get my pants and boxers pulled down. I let her get everything down around my ankles but pushed her back as I held my dick in my hands.

“Now I’m sorry I made you horny,” I told her as I made sure all four girls saw the seven inches of dick I was holding. “I’m of average circumference, so it won’t stretch you open how a fat dick would. You can probably take most of the length too, but this isn’t the time or place to screw the first time.”

It didn’t stop her, so I kicked one foot free of my shorts and boxer, grabbed her robe tie, and the one from her roommate’s robe. Mary had the panties and bra back on before she made it close enough to touch my dick. A quick spin around had her robe on and tied around her waist. Her hands I bound with her roommate’s robe belt, which I also hooked around the rung of the chair she had been in earlier. As I finished tying her wrists, I put her cell phone back in her hand.

I did make out with her quickly before pushing the tiny bit of energy into her head that she needed to trigger the big orgasm she was waiting to have when she reached for my dick. Both of my hands were behind my back the whole time we made out because I didn’t want anyone saying I molested her while tied up.

I felt a bit bad about causing her to cum without her knowing how, without me touching her anywhere, so I untied her hands and moved to where she could check out my dick if she wanted to. I could see that she did, but was unsure, at least until I started to step back to get dressed. That got her reaching out to cradle it like it was breakable.

Karen reminded me that she had a class in fifteen minutes. Her books were back in her room.

Surprising everyone, Mary, first kissed the head on my dick, ran her tongue around it a few times, and then took two inches of my still limp dick in her mouth. She subconsciously jacked my dick as she sucked me until I was hard. In the blink of an eye, she had one hand pulling her panties to the side and the other pushing my dick down for her to rub over her clit. Mary used the hand holding her panties to the side to hide that she was pushing my dick down to slide two inches of my dick inside her as she thrust her hips like she was grinding her clit against my it. I didn’t say a word, but I did feel it when she shoved up hard enough to have three inches inside her when she came.

“Get out, David. Like right now, or I will have to scream, except it will be a scream begging you to take my virginity with that big monster. I don’t have any willpower left to resist begging you for it and trying to figure out how to rape you,” Mary said as she let her panties slid back over her mound after she used her robe to wipe off the blood from where my dick tore through hymen.

She pulled me down to whisper in my ear and said, “If Karen leaves you with blue balls, and you don’t want to jack off tonight, sneak down to my room. That is the best thing I have ever felt in my life, and you didn’t give away that I had you inside me.”

Karen almost pulled me out by my dick before realizing I pulled on my shorts and underwear on first. I had Mary’s roommate come down to where I dropped my bags. I fished out a two-pack of boxer-briefs that would fit her nicely. I joked that she could toss out the ones from her brother unless she had some other reason why she was keeping them. She joked back that she was from Rhode Island, not a southern state.

When Karen locked the door behind us, I pushed her onto the nearest bed, pulled her shorts and panties off with my face buried in her hairy muff. My tongue worked its magic as my middle finger carefully worked through the hole in her cherry to search out her g-spot. I’m not exactly sure I found it because she was in the middle of a massive orgasm when her watch beeped for her to go to class. I grabbed the nearest washcloth, wet it using a nearby water bottle, washed her pussy clean, and then lifted her legs like I was changing a baby to put on the body powder that she had in her shower basket. It was a good thing that I could dress a girl quickly, or she would have been late to class. As it was, I had her get on my back to run as she navigated. I could feel the heat of her pussy against where my hands were behind me, so I slipped my thumb inside her panties to rub over her clit each time she dropped down from bouncing as we ran.

Karen is very contentious about being early to class. We had arrived seven minutes before class started. She excused herself to the bathroom after telling me to take off the dorm escort-required badge. The grin her face made her seem to glow with pure happiness, not having a care in the world.

“I fibbed a bit when I was getting you access to the dorm. My friends said you were an amazing guy who I could trust wouldn’t do anything to me that I didn’t want or ask you to do. Mary has feared guys since she got here last fall. Did she let you enter her? It looked like the angle wasn’t high enough to rub against her clit,” Karen inquired.

I looked her in the eyes as I said, “If you want to talk with me about my going down on you to take the edge off or making you cum while bouncing on my back as we ran over here, fine. I don’t know what you’re talking about me doing with Mary. I only had minimal contact with her breasts as I helped settle them into her bra properly. I’ve done that hundreds of times when fitting bras on small chested women and girls to ensure they had the right fit. Now, if Mary wants to talk to you about how that made her feel, then you two have a blast having girl talk. If she says something wild, you can’t call her a liar by saying I said something different.”

She hugged me and kissed me on the lips before whispering in my ear, “They educated me about that aspect of you too, David. It is a blessing to know that I have real friends here who didn’t lie to me about knowing this fictional guy back home who is as amazing as you are real. We better get some seats. Not many students bother to show up to his class this time of day. They usually go to the second lecture he does at two. If not for the required language lab, I doubt any students would pass his classes. He doesn’t even require us to buy any textbooks.”

We sat three rows back from the front. There were maybe fifteen students in a class Karen told me had three-hundred students signed up.